연구동향 분석
박사

Chiral oxazaborolidinium ion activated carboxylic acids and aldimines : catalytic enantioselective protonation/nucleophilic addition, strecker and povarov reactions

Kang, Kitae 2020년

논문상세정보
인용/피인용
' Chiral oxazaborolidinium ion activated carboxylic acids and aldimines : catalytic enantioselective protonation/nucleophilic addition, strecker and povarov reactions' 의 주제별 논문영향력
논문영향력 선정 방법
논문영향력 요약
주제
  • Oxazaborolidinium ion
  • Povarov
  • Strecker
  • asymmetric catalysis
  • boron
  • protonation/nucleophilic addition
동일주제 총논문수 논문피인용 총횟수 주제별 논문영향력의 평균
30 0

0.0%

' Chiral oxazaborolidinium ion activated carboxylic acids and aldimines : catalytic enantioselective protonation/nucleophilic addition, strecker and povarov reactions' 의 참고문헌

  • see : Maruoka, 107 , 4584 . (C )Cativiela ,C. ;
    K. ; Ooi ,Sansano , J. M. Chem . Rev ., 569 . (
  • W. D. ; Izzo , J . A. ; Vetticatt , M. J. J . Am
    aG. ; Huang , R. H. ; Wulff. ( b )
  • Soloshonok , V. A. , Izawa
    K. , Eds
  • Perkin Trans . 1 , 1972 , 1597 . ( c ) Baker , T. M. ; Bodwell ,
    b ) Youngson , G. W. ; Watson , M. B. J. Chem . Soc.; Edwards , A.
  • Leete , E. J . Am .Chem . Soc . 1960 , 82 ,
    A. ; Leete , E. JJ. ; Liu ,
  • J. J. Org
    64 , 6462 . [1999]
  • J. J . Am . Chem .
    ;) Payette , J.
  • Ishihara , K. ; Yamamoto , H. AcidCatalysis in modern organic synthesis
    , H Chemical Record. Chem .
  • I. ; Shepperson , R. ; Slaughter ,
    C. ; Mart & nez del Campo ,Int . Ed .
  • Deloux , L. ; Srebnik , M.Chem . Rev . 1993 ,
    H.T. ; Morita ,
  • D. H. ; Corey , E. J.
    124125 , 6388 [2002]
  • D-Amino Acids in Chemistry , Life Sciences , and Biotechnology
    47 , 199 . ( b [1978]
  • Corey , E.
    41 , 1650 . [2002]
  • Bello , D. ; Ramn , R.
    . 2010 , 14 , 332. ( c ) Glushkov , V. A. ; Tolstikov , A. G. Russ . Chem77 , 137 . [2008]
  • ; Borre , K. ; Axenov , K. ; Ko ? tai , B. ;
    , 8686 . ( b ) Lindqvist ,, I. ; Repo
  • 92 , 935 . ( c ) Paradowska , J. ; Stodulski , M. ; Mlynarski , J. Angew . Chem.
    6548 , 4288 .
  • 6 ) ( a ) Liu , G. ; Zhang , D. Li , J. ; Xu , G. ; Sun , J. Org . Biomol
    Liu , Y. ;( c [1301]
  • 3 ) ( a ) Allwood , D. M.
    D. C. ; Ley , S.Z. ; Ge , R. ; Xiao , Q. ; Zhang , Y.Ed . 2013 ,
  • 17 ) Than , M. S.
    10 , 135 [2008]
  • . Enolsilane : Senapati
    OrgS. I. ; Hwang
  • . 2011 , 111 , 6947 . Merino , P. ; Marques-Lopez , E. ; Tejero , T. ; Herrera , R. P. Tetrahedron 2009 , 65 ,
    . Chem . Int
  • , 2745 . Gao
    reactions;Y. ; Ryu ,
  • (9) Zheng, H.; Hall, D. G. Aldrichimica Acta 2014, 47, 41.
    47 , 41 . [2014]
  • (9) Mohr, J. T.; Hong, A. Y.; Stoltz, B. M. Nat. Chem. 2009, 1, 359.
  • (8) Tringuelli, F.; Taticchi, A. The Diels?Alder Reaction. Selected Practical Methods; John Wiley: London, 2002.
  • (8) Strecker, A. Ann. Chem. Pharm. 1850, 75, 27.
  • (8) Dimitrijevic, E.; Taylor, M. S. ACS Catal. 2013, 3, 945.
  • (8) (a) Yanagisawa, A.; Yamamoto, H. in Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.: Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.), Springer, Heidelberg, 1999, pp. 1295?1306; (b) Duhamel, L.; Duhamel, P.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2004, 15, 3653. (c) Oudeyer, S.; BriHre, J.-F.; Levacher, V. Eur. J. Org. Chem. 2014, 6103 (e) Phelan, J. P.; Ellman, J. A. Beilstein J. Org. Chem. 2016, 12, 1203.
  • (7) Lawson, J. R.; Melen, R. L. Inorg. Chem. 2017, 56, 8627.
  • (7) (a) Regitz, M.; Maas, G. Diazo Compounds: Properties and Synthesis, Academic Press, Orlando, 1986, chap. 3. For reviews on reactions of diazo compounds, see: (b) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811. (c) Johnston, J. N.; Muchalski, H. T.; Troyer, L. Angew. Chem. Int. Ed. 2010, 49, 2290.
  • (6) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem. Int. Ed. 2002, 41, 1669.
  • (6) Melen, R. L. Chem. Commun. 2014, 50, 1161.
  • (6) Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem. Int. Ed. 2001, 40, 1896.
  • (5) Kumar, A. Chem. Rev. 2001, 101, 1.
  • (5) (a) Schlotterbeck, F. Ber. Dtsch. Chem. Ges. 1907, 40, 1826. (b) Schlotterbeck, F. Ber. Dtsch. Chem. Ges. 1907, 40, 3000. (c) Meyer, H. Monatsh. Chem. 1905, 26, 1295. (d) Pechmann, H. Ber. Dtsch. Chem. Ges. 1895, 28, 855. (e) Buchner, E.; Curtius, T. Ber. Dtsch. Chem. Ges. 1885, 18, 2371.
  • (5) (a) Erker, G. Dalton Trans. 2005, 1883. (b) Feng, X.; Du, H. Tetrahedron Lett. 2014, 55, 6959. (c) Oestreich, M.; Hermeke, J.; Mohr, J. Chem. Soc. Rev. 2015, 44, 2202. (d) Stephan, D. W.; Erker, G. Angew. Chem. Int. Ed. 2015, 54, 6400.
  • (4) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
  • (4) Groger, H. Chem. Rev. 2003, 103, 2795.
  • (4) (a) Smith, P. A. S.; Baer, D. R. Org. React. 1960, 11, 157. (b) Wovkulich, P. M. Skeletal Reorganizations: Chain Extension and Ring Expansion. In Comprehensive Organic Synthesis, Oxford, 1991, 844.
  • (39) (a) Fleischmann, M.; Drettwan, D.; Sugiono, E.; Rueping, M.; Gschwind, R. M. Angew.Chem. Int. Ed. 2011, 50, 6364. (b) Gridnev, I. D.; Kouchi, M.; Sorimachi, K.; Terada, M. Tetrahedron Lett. 2007, 48, 497. (c) Huang, J.;Corey, E. J. Org. Lett. 2004, 6, 5027.
    497 . ( c
  • (38) Huber, J. D.; Leighton, J. L. J. Am.Chem. Soc. 2007, 129, 14552.
    129 , 14552 . [2007]
  • (37) (a) Sadhukhan, A.; Sahu, D.; Ganguly, B.; Khan, N. H.; Kureshy, R. I.; Abdi, S. H. R.; Suresh, E.; Bajaj, H.C.Chem. Eur. J. 2013, 19, 14224. (b) Roben,C.; Souto, J. A.; Gonzalez, Y.; Lishchynskyi, A.; Muniz, K. Angew.Chem. Int. Ed. 2011, 50, 9478. (c) Bergel, F.; Butler, J. J.Chem. Soc. 1961, 4047.
    ;. 2013 , 19 , 14224 . (
  • (36) (a) Liu, L.-J.; Chen, L.-J.; Li, P.; Li, X.-B.; Liu, J.-T. J. Org. Chem. 2011, 76, 4675. (b) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Chem. Pharm. Bull. 2000, 48, 1586.
  • (35) Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
  • (34) For selected examples of enantioselective Strecker reaction with Bu3SnCN, see: (a) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am.Chem. Soc. 2000, 122, 762. (b) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew.Chem. Int. Ed. 1998, 37, 3186.
    . Soc . 2000 , 122 , 762 . ( b ) Ishitani , H. ;. Ed . 1998
  • (34) Akiyama, T.; Morita, H.; Fuchibe, K. J. Am.Chem. Soc. 2006, 128, 13070.
    128 , 13070 [2006]
  • (33) For 1H NMR analysis of the pre-transition-state assembly 3, see the Supporting Information.
  • (33) (a) Ryu, D. H.; Lee, T. W.;Corey, E. J. J. Am.Chem. Soc. 2002, 124, 9992. (b) Ryu, D. H.;Corey, E. J. J. Am.Chem. Soc. 2003, 125, 6388. (c) Ryu, D. H.; Zhou, G.;Corey, E. J. J. Am.Chem. Soc. 2004, 126, 4800. (d) Ryu, D. H.; Zhou, G.;Corey, E. J. Org. Lett. 2005, 7, 1633.
    ;H.H. ; Zhou ,
  • (32) Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986.
    327 , 986 [2010]
  • (32) The activation modes of ion pairing in complex 3 cannot be ruled out. see: Hu, G.; Gupta, A. K.; Huang, R. H.; Mukherjee, M.; Wulff, W. D. J. Am. Chem. Soc. 2010, 132, 14669.
  • (31) Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357.
    37 , 7357 . [1996]
  • (31) For selected review on hydrogen-bonding in aldimine activation, see: (a) Parmar, D.; Sugiono, E.; Raja, S.; Rueping, M.Chem. Rev. 2014, 114, 9047. For selected examples of hydrogen-bonding in aldimine activation, see: (b) Fleischmann, M.; Drettwan, D.; Sugiono, E.; Rueping, M.; Gschwind, R. M. Angew.Chem. Int. Ed. 2011, 50, 6364. (c) Gridnev, I. D.; Kouchi, M.; Sorimachi, K.; Terada, M. Tetrahedron Lett. 2007, 48, 497. (d) Huang, J.;Corey, E. J. Org. Lett. 2004, 6, 5027.
    E. ; Rueping ,
  • (30) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195.
  • (30) For synthesis of COBI catalyst 1c, see: Canales, E.; Corey, E. J. Org. Lett. 2008, 10, 3271.
  • (3) Sauer, J.; Sustmann, R. Angew. Chem., Int. Ed. 1989, 19, 779.
  • (3) (a) Takao, K. I.; Munakata, R.; Tadano, K. I.Chem. Rev. 2005, 105, 4779. (b) Winkler, J. D.Chem. Rev. 1996, 96, 167. (c) Boger, D. A.Chem. Rev. 1986, 86, 781.
    10596 , 167 . ( c ) Boger86 , 781 .
  • (3) (a) Roscales, S.; Csaky, A. G. Chem.Soc. Rev. 2014, 43, 8215. (b) Flanigan, D. M.; Romanov-Michailidis, F.; White, N. A.; Rovis, T. Chem.Rev. 2015, 115, 9307. (c) Bisogno, F. R.; Lopez-Vidal, M. G.; de Gonzalo, G. Adv. Synth. Catal. 2017, 359, 2026.
  • (29) Enantioselective Strecker reaction between o-hydroxyphenyl aldimine and TMSCN provided the メ-aminonitrile 4 as a major product in 88% yield and 74% ee.
  • (28) For selected reviews onCatalytic enantioselective Strecker reaction, see: (a) Liu, Y.-L.; Zhou, J. Synthesis 2015, 47, 1210. (b) Wang, J.; Liu, X.; Feng, X.Chem. Rev. 2011, 111, 6947. For selected examples ofCatalytic enantioselective Strecker reaction, see:Chiral Lewis acidCatalysts: (c) Zhao, J.; Liu, X.; Luo, W.; Xie, M.; Lin, L.; Feng, X. Angew.Chem. Int. Ed. 2013, 52, 3473.Chiral organocatalysts: (d) Saravanan, S.; Khan, N. H.; Kureshy, R. I.; Abdi, S. H. R.; Bajaj, H.C. ACSCatal. 2013, 3, 2873. (e) Yan, H.; Oh, J. S.; Lee, J.-W.; Song,C. E. Nat.Commun. 2012, 3, 1. (f) Zuend, S. J.;Coughlin, M. P.; Lalonde, M. P.; Jacobsen, E. N. Nature 2009, 461, 968. (g) Wang, J.; Hu, X.; Jiang, J.; Gou, S.; Huang, X.; Liu, X.; Feng, X. Angew.Chem. Int. Ed. 2007, 46, 8468.
    chiral Lewis acid catalysts
  • (28) Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225.
  • (27) Rogers, J. L.; Ernat, J. J.; Yung, H.; Mohan, R. S. Catal. Commun. 2009, 10, 625.
  • (27) For the development of COBI catalysts see: (a) Corey, E. J. Angew. Chem. Int. Ed. 2009, 48, 2100. For selected examples of enantioselective cyanosilylation with COBI catalyst, see: (b) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384. (c) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8106.
  • (26) Sridharan, V.; Avendano, C.; Menendez, J. C. Synthesis 2008, 1039.
  • (26) Enantioselective Strecker reaction between N-benzyl-benzylidene imine and HCN provided chiral amine product 4 as a major product in ~73% ee. For the asymmetric hydrocyanation of imines with oxazaborolidines, see: Berkessel, A.; Mukherjee, S.; Lex, J. Synlett. 2006, 1, 41.
  • (25) Das, B.; Reddy, M. R.; Reddy, V. S.; Ramu, R.Chem. Lett. 2004, 33, 1526.
    33 , 1526 . [2004]
  • (25) Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2009, 131, 15118.
  • (24) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762.
  • (24) (a) Wang, J.; Hu, X.; Jiang, J.; Gou, S.; Huang, X.; Liu, X.; Feng, X. Angew. Chem. Int. Ed. 2007, 46, 8468. (b) Wang, J.; Wang, W.; Li, W.; Hu, X.; Shen, K.; Tan, C.; Liu, X.; Feng, X. Chem. Eur. J. 2009, 15, 11642.
  • (23) (a) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. Int. Ed. 2000, 39, 1650. (b) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634.
  • (23) (a) Jadhav, A. M.; Pagar, V. V.; Liu, R.-S. Angew.Chem. Int. Ed. 2012, 51, 11809. (b)Chen,C.-N.; Liu, R.-S. Angew.Chem. Int. Ed. 2019, 131, 9831.
    51 , 11809 . ( b131 , 9831 [2012]
  • (23) (a) Al-Zoubi, R. M.; Marion, O.; Hall, D. G. Angew.Chem. Int. Ed. 2008, 47, 2876. (b) Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org.Chem. 1996, 61, 4196.
    47 , 2876 . ( b61 , 4196 . [2008]
  • (22) (a) Byrne, J. J.; Chavarot, M.; Chavant, P.-Y.; Vallee, Y. Tetrahedron Lett. 2000, 41, 873. (b) Chavarot, M.; Byrne, J. J.; Chavant, P.-Y.; Vallee, Y. Tetrahedron: Asymmetry 2001, 12, 1147.
  • (22) (a) Barluenga, J.; Mendoza, A.; Rodriguez, F.; Fananas, F. J. Angew.Chem. Int. Ed. 2008, 47, 7044. (b) Barluenga, J.; Mendoza, A.; Rodriguez, F.; Fananas, F. J.Chem. Eur. J. 2008, 14, 10892. (c)Calleja, J.; Gonzalez-Perez, A. B.; Lera, A. R.; Alvarez, R.; Fananas, F. J.; Rodriguez, F.Chem. Sci. 2014, 5, 996. (d) Wang,C.; Han, Z. Y.; Luo, H. W.; Gong, L. Z. Org. Lett. 2010, 12, 2266. (e) Dagousset, G.; Zhu, J.; Masson, G. J. Am.Chem. Soc. 2011, 133, 14804. (f) Bao, M.; Lu, W.; Su, H.; Qiu, L.; Xu, X. A Org. Biomol.Chem. 2018, 16, 3258.
    2008 , 47 , 7044 .. ( c )
  • (21) Selected recent examples: (a) Akiyama, T.; Morita, H.; Fuchibe, K. J. Am.Chem. Soc. 2006, 128, 13070. (b) Xu, H.; Zuend, S. J.; Woll, M. G.; Tao, Y.; Jacobson, E. N. Science 2010, 327, 986. (c) He, L.; Bekkaye, M.; Retailleau, P.; Masson, G. Org. Lett. 2012, 14, 3158. (d) Shi, F.; Xing, G. J.; Tao, Z. L.; Luo, S. W.; Tu, S. J.; Gong, L. Z. J. Org.Chem. 2012, 77, 6970. (e)Caruana, L.; Fochi, M.; Ranieri, S.; Mazzanti, A.; Bernardi, L.Chem.Commun. 2013, 49, 880. (f)Chen, Z.; Wang, B.; Wang, Z.; Zhu, G.; Sun, J. Angew.Chem. Int. Ed. 2013, 52, 2027. (g) Min,C.; Mittal, N.; Sun, D. X.; Seidel, D. Angew.Chem. Int. Ed. 2013, 52, 14084. (h) Luo,C.; Huang, Y. A J. Am.Chem. Soc. 2013, 135, 8193.
    H. ; Zuend ,. ( c )
  • (21) Peng,C.; Wang, Y.; Wang, J. J. Am.Chem. Soc. 2008, 130, 1566.
    130 , 1566 [2008]
  • (21) (a) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew.Chem. Int. Ed. 1998, 37, 3186. (b) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am.Chem. Soc. 2000, 122, 762.
    37122 , 762 [1998]
  • (20) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
  • (20) Selected recent examples: (a) Xie, M. S.;Chen, X. H.; Zhu, Y.; Gao, B.; Lin, L. L.; Liu, X. H.; Feng, X. M. Angew.Chem., Int. Ed. 2010, 49, 3799. (b) Yu, J.; Jiang, H.; Zhou, Y.; Luo, S.; Gong, L. Z. Angew.Chem., Int. Ed. 2015, 54, 11209.
    ,; Zhou , Y.
  • (20) For selected reviews on ヰ-ヰ interaction, see: (a) Waters, M. L. Curr. Opin. Chem. Biol. 2002, 6, 736. (b) Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2, 2001, 651. (c) Salonen, L. M.; Ellermann, M.; Diederich, F. Angew. Chem., Int. Ed. 2011, 50, 4808. For selected paper on ヰ-ヰ interaction, see: (d) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
  • (20) For selected examples of enantioselective tandem reactions withCOBICatalyst, see:Cyclopropanation: (a) Shim, S. Y.;Choi, Y.; Ryu, D. H. J. Am.Chem. Soc. 2018, 140, 11184. (b) Shim, S. Y.;Cho, S. M.; Venkateswarlu, A.; Ryu, D. H. Angew.Chem., Int. Ed. 2017, 56, 8663. (c) Shim, S. Y.; Kim, J. Y.; Nam, M.; Hwang, G.-S.; Ryu, D. H. Org. Lett. 2016, 18, 160. (d) Gao, L.; Hwang, G.-S.; Ryu, D. H. J. Am.Chem. Soc. 2011, 133, 20708. Protonation/nucleophilic addition: (e) Kang, K.-T.; Kim, S. T.; Hwang, G.-S.; Ryu, D. H. Angew.Chem., Int. Ed. 2017, 56, 3977.C?H functionalization: (f) Lee, S. I.; Hwang, G.-S.; Ryu, D. H. J. Am.Chem. Soc. 2013, 135, 7126. Roskamp reactions: (g) Kim, J. Y.; Kang, B.C.; Ryu, D. H. Org. Lett. 2017, 19, 5936. (h) Shin, S. H.; Baek, E. H.; Hwang, G.-S.; Ryu, D. H. Org. Lett. 2015, 17, 4746. (i) Kang, B.C.; Nam, D. G.; Hwang, G.-S.; Ryu, D. H. Org. Lett. 2015, 17, 4810. (j) Gao, L.; Kang, B.C.; Ryu, D. H. J. Am.Chem. Soc. 2013, 135, 14556. (k) Gao, L.; Kang, B.C.; Hwang, G.-S.; Ryu, D. H. Angew.Chem., Int. Ed. 2012, 51, 8322.
    D. H. J . Am ., D. H. Angew
  • (2) Otera, J., Ed. Modern Carbonyl Chemistry; Wiley-VCH: Weinheim, Germany, 2000.
  • (2) Needleman, S. B.; Chang Kuo, M. C. Chem. Rev. 1962, 62, 405.
  • (2) (a) Kirmse, W. Eur. J. Org.Chem. 2002, 2193. (b) Arndt, F.; Eistert, B. Ber. Dtsch.Chem. Ges. B 1935, 68, 200.
    68 , 200 . [2002]
  • (2) (a) Akiyama, T. Science of Synthesis : Asymmetric Organocatalysis, Vol. 2 (Ed. K. Maruoka), Thieme, Stuttgart, 2012, pp.169?217. (b) Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626. (c) Ma, J.? A. Angew. Chem. Int. Ed. 2003, 42, 4290. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
  • (19) Liu, D.; Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 8160.
  • (19) Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910.
  • (18) Li, P.; Mai, K.; Trushenski, J.; Wu, G. Amino Acids 2009, 37, 43.
    37 , 43 . [2009]
  • (18) For reviews: (a) Forero, J. S. B.; Junior, J. J.; da Silva, F. M.Curr. Org. Synth. 2016, 13, 157. (b) Wang, Y.; Lu, H.; Xu, P. Acc.Chem. Res. 2015, 48, 1832. (c) Muthukrishnan, I.; Sridharan, V.; Menendez, J.C.Chem. Rev. 2019, 119, 5057.
    Junior , J., Y. ; Lu , H. ; Xu , P. Acc . Chem . Res .Muthukrishnan , I. ;
  • (17) (a) Burai, R.; Ramesh, C.; Shorty, M.; Curpan, R.; Bologa, C.; Sklar, L. A.; Oprea, T.; Prossnitz, E. R.; Arterburn, J. B. Org. Biomol. Chem. 2010, 8, 2252. (b) Gore, V. K.; Ma, V. V.; Yin, R.; Ligutti, J.; Immke, D.; Doherty, E. M.; Norman, M. H. Bioorg. Med. Chem. Lett. 2010, 20, 3573. (c) Ramesh, C.; Nayak, T. K.; Burai, R.; Dennis, M. K.; Hathaway, H. J.; Sklar, L. A.; Prossnitz, E. R.; Arterburn, J. B. J. Med. Chem. 2010, 53, 1004.
  • (16) For reviews: (a) Barluenga, J.; Rodriguez, F.; Fananas, F. J. Chem. Asian J. 2009, 4, 1036. (b) Sridharan, V.; Suryavanshi, P. A.; Menendez, J. C. Chem. Rev. 2011, 111, 7157. (c) Zhang, F.; Ma, S. Curr. Drug Targets 2018, 19, 1148.
  • (16) (a)Corey, E. J. Angew.Chem., Int. Ed. 2009, 48, 2100. (b) Yamamoto, H.; Futatsugi, K. Angew.Chem., Int. Ed. 2005, 44, 1924. (c) Shim, S. Y.; Ryu, D. H. Acc.Chem. Res. 2019, 52, 2349.
    2009 , 48 , 2100 .2019 , 52 ,
  • (16) (a) Massey, K. A.; Blakeslee, C. H.; Pitkow, H. S. Amino Acids 1997, 14, 271. (b) Elango, R.; Ball, R. O.; Pencharz, P. B. Amino Acids 2009, 37, 19.
  • (15) Tan, F.; Liu, X.; Hao, X.; Tang, Y.; Lin, L.; Feng, X. ACSCatal. 2016, 6, 6930
    6 , 6930 [2016]
  • (15) Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656.
  • (15) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808.
  • (14) Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSR, Ser. Khim. 1964, 2221.
  • (14) For reviews, see: (a) Opatz, T. Synthesis 2009, 1941. (b) Otto, N.; Opatz, T. Chem. Eur. J. 2014, 20, 13064.
  • (14) (a)Corey, E. J. Angew.Chem. Int. Ed. 2009, 48, 2100. (b) Mukherjee, S.;Corey, E. J. Aldrichimica Acta 2010, 43, 49.
    4843 , 49 . [2009]
  • (13) Grigos, V. I.; Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSR, Ser. Khim. 1965, 2163.
  • (13) For selected reviews, see: (a) Ye, T.; Mckervey, M. A.Chem. Rev. 1994, 94, 1091. (b)Coppola, G. M.; Schuster, H. F. メ-Hydroxy Acids in Enantioselective synthesis; Wiley-VCH: Weinheim, 1997; pp 1?513. (c) Doyle, M. P.; Mckervey, M. A.; Ye, T. ModernCatalytic Methods for Organic Synthesis with DiazoCompounds; Wiley: New York, 1998;Chapters 8.3 and 8.4. (d) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577. (e) Zhu, S.-F.; Zhou, Q.-L. Acc.Chem. Res. 2012, 45, 1365. For selected enantioselective examples, see: (f) Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V. J. Org.Chem. 1997, 62, 1630. (g) Maier, T.C.; Fu, G.C. J. Am.Chem. Soc. 2006, 128, 4594. (h)Chen,C.; Zhu, S.-F.; Liu, B.; Wang, L.-X.; Zhou, Q.-L. J. Am.Chem. Soc. 2007, 129, 12616. (i) Zhu, S.-F.;Chen,C.;Cai, Y.; Zhou, Q.-L. Angew.Chem., Int. Ed. 2008, 47, 932. (j) Zhu, S.-F.;Cai, Y.; Mao, H.X.; Xie, J.-H.; Zhou, Q.-L. Nat.Chem. 2010, 2, 546. (k) Song, X.-G.; Zhu, S.-F.; Xie, X.-L.; Zhou, Q.-L. Angew.Chem., Int. Ed. 2013, 52, 2555. (l) Xie, X.-L.; Zhu, S.-F.; Guo, J.-X.;Cai, Y.; Zhou, Q.-L. Angew.Chem., Int. Ed. 2014, 53, 2978.
    ; Mckervey , M. [1994]
  • (12) Pracejus, H. Justus Liebigs Ann. Chem. 1960, 634, 9.
  • (12) Povarov, L. S.; Grigos, V. I.; Karakhanov, R. A.; Mikhailov, B. M. Izv. Akad. Nauk SSR, Ser. Khim. 1964, 179.
  • (12) Lipscomb, W. N. Science 1977, 196, 1047.
  • (12) For a review, see: Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359.
  • (11) Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izv. Akad. Nauk SSR, Ser. Khim. 1963, 2039.
  • (11) (a) Repka, L. M.; Ni, J.; Reisman, S. E. J. Am.Chem. Soc. 2010, 132, 14418. (b) Wang, M. H.;Cohen, D. T.; Schwamb,C. B.; Mishra, R. K.; Scheidt, K. A. J. Am.Chem. Soc. 2015, 137, 5891. (c) Daniels, B. E.; Ni, J.; Reisman, S. E. Angew.Chem. Int. Ed. 2016, 55, 3398. (d) Roy, A.; Bhat, B. A.; Lepore, S. D.; Org. Lett. 2016, 18, 1230. (e) Das, A.; Ayad, S. Hanson, K. Org. Lett. 2016, 18, 5416.
    D. T. ; SchwambSoc . 2015 ,
  • (11) (a) Payette, J. N.; Yamamoto, H. Borate and boronic acid derivatives asCatalysts in organic synthesis. In Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials (Ed.: D. G. Hall), Wiley, 2011, Vol. 2,Chapter 12. (b) Meng, W.; Feng, X.; Du, H. Acc.Chem. Res. 2018, 51, 191. (c) Sgsse, L.; Vogler, M.; Mewald, M.; Kemper, B.; Irran, E.; Oestreich, M. Angew.Chem. Int. Ed. 2018, 57, 11441. (d) Kumar, S. N.; Yu, I. F.;Chein, R.-J. Org. Lett. 2017, 19, 22. (e) Thirupathi, B.; Breitler, S.; Reddy, K. M.;Corey, E. J. J. Am.Chem. Soc. 2016, 138, 10842. (f) Hatano, M.; Hayashi, K.; Sakamoto, T.; Makino, Y.; Ishihara, K. Synlett. 2016, 27, 1061. (g) Dimitrijevic, E.; Taylor, M. S.; ACSCatal. 2013, 3, 945. (h) De Vries, T. S.; Prokofjevs, A.; Vedejs, E.Chem. Rev. 2012, 112, 4246. (i) Ryu, D. H.; Zhou,G.;Corey, E. J. J. Am.Chem. Soc. 2004, 126, 4800. (j) Deloux, L.; Srebnik, M.Chem. Rev. 1993, 93, 763.
    and) , Wiley , 2011 , Vol . 2 , Chapter 12Feng , X. ;
  • (11) (a) Gao, L.; Kang, B. C.; Hwang, G.-S.; Ryu, D. H. Angew. Chem. Int. Ed. 2012, 51, 8322. (b) Lee, S. I.; Hwang, G.-S.; Ryu, D. H. J. Am. Chem. Soc. 2013, 135, 7126. (c) Gao, L.; Kang, B. C.; Ryu, D. H. J. Am. Chem. Soc. 2013, 135, 14556. (d) Shin, S. H.; Baek, E. H.; Hwang, G.-S.; Ryu, D. H. Org. Lett. 2015, 17, 4746. (e) Kang, B. C.; Nam, D. G.; Hwang, G.-S.; Ryu, D. H.; Org. Lett. 2015, 17, 4810. (f) Shim, S. Y.; Kim, J. Y.; Nam, M.; Hwang, G.-S.; Ryu, D. H. Org. Lett. 2016, 18, 160.
  • (10) Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSR, Ser. Khim. 1963, 953.
  • (10) Mohr, J. T. Krout, M. R. & Stoltz, B. M. Nature 2008, 455, 323.
  • (10) (a) Enders, D.; Shilvock, J. P.Chem. Soc. Rev. 2000, 29, 359. (b) Opatz, T. Synthesis 2009, 1941.
    29 , 359 . ( b ) Opatz , T. Synthesis
  • (10) (a) De Vries, T. S.; Prokofjevs, A.; Vedejs, E. Chem. Rev. 2012, 112, 4246. (b) Eisenberger, P.; Crudden, C. M. Dalton Trans. 2017, 46, 4874.
  • (1) Yamamoto, H., Ed. Lewis Acids in Organic Synthesis; Weinheim, Wiley-VCH, 2000.
  • (1) Smith, M. B. Organic Synthesis, 2nd ed.; Mc Graw-Hill: New York, NY, 2002; pp 844?849.
  • (1) For selected reviews on enantioselective nucleophilic addition reactions ofCarbonylCompounds usingChiral boron Lewis acidCatalysts see: (a) North, M.; Usanov, D. L.; Young,C.Chem. Rev. 2008, 108, 5146. For selected examples usingCarbonylCompounds, see: (b) Gupta, A. K.; Yin, X.; Mukherjee, M.; Desai, A. A.; Mohammadlou, A.; Jurewicz, K.; Wulff, W. D. Angew.Chem. Int. Ed. 2019, 58, 3361. (c) Shang, M.;Cao, M.; Wang, Q.; Wasa, M. Angew.Chem. Int. Ed. 2017, 56, 13338. (d) Su?sse, L.; Hermeke, J.; Oestreich, M. J. Am.Chem. Soc. 2016, 138, 6940. (e) Bang, J.; Kim, H.; Kim, J.; Yu,C.-M. Org. Lett. 2015, 17, 1573. (f) Ren, H.; Wulff, W. D. J. Am.Chem. Soc. 2011, 133, 5656.
    compounds2008 , 108 ,X. ; Mukherjee ,
  • (1) (a)Candeias, N. R.; Paterna, R.; Gois, P. M. P.Chem. Rev. 2016, 116, 2937. (b) Ford, A.; Miel, H.; Ring, A.; Slattery,C. N.; Maguire, A. R.; McKervey, M. A.Chem. Rev. 2015, 115, 9981. (c) Zhang, Y.; Wang, J.Chem.Commun. 2009, 5350. (d) Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577.
    b, 9981 . (