메뉴 건너뛰기




Volumn 130, Issue 36, 2008, Pages 12031-12037

Organocatalytic asymmetric synthesis of α,α-disubstituted α-amino acids and derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALDEHYDES; AMIDES; AMINATION; AMINES; AMINO ACIDS; AROMATIC COMPOUNDS; ARSENIC COMPOUNDS; COMPLEXATION; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; ETHERS; HYDROGEN; HYDROGEN BONDS; ORGANIC ACIDS; SILANES; STEREOSELECTIVITY;

EID: 51749120761     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja804567h     Document Type: Article
Times cited : (170)

References (99)
  • 2
    • 0032561221 scopus 로고    scopus 로고
    • For reviews on synthesis of α,α-disubstituted α-amino acids, see, for example:a
    • For reviews on synthesis of α,α-disubstituted α-amino acids, see, for example:(a) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3517
    • Cativiela, C.1    Díaz-de-Villegas, M.D.2
  • 11
    • 36849051865 scopus 로고    scopus 로고
    • For a recent review on catalytic asymmetric synthesis of α-amino acids, see
    • For a recent review on catalytic asymmetric synthesis of α-amino acids, see:Nájera, C.; Sansano, J. M. Chem. Rev. 2007, 107, 4584.
    • (2007) Chem. Rev , vol.107 , pp. 4584
    • Nájera, C.1    Sansano, J.M.2
  • 12
  • 14
    • 41249092756 scopus 로고    scopus 로고
    • For a highlight of the Strecker reaction, see:(a) Connon, S. J. Angew. Chem., Int. Ed. 2008, 47, 1176.
    • For a highlight of the Strecker reaction, see:(a) Connon, S. J. Angew. Chem., Int. Ed. 2008, 47, 1176.
  • 15
    • 34447272888 scopus 로고    scopus 로고
    • For recent reviews of phase-transfer catalysis, see:a
    • For recent reviews of phase-transfer catalysis, see:(a) Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 4222.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 4222
    • Ooi, T.1    Maruoka, K.2
  • 17
    • 34547460624 scopus 로고    scopus 로고
    • Fisk, J. S.; Mosey, R. A.; Tepe, J. J. Chem. Soc. Rev. 2007, 36, 1432. See also ref 2d.
    • Fisk, J. S.; Mosey, R. A.; Tepe, J. J. Chem. Soc. Rev. 2007, 36, 1432. See also ref 2d.
  • 22
    • 6044269452 scopus 로고    scopus 로고
    • For recent reviews of organocatalysis, see e.g.:(a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
    • For recent reviews of organocatalysis, see e.g.:(a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
  • 24
    • 51749089778 scopus 로고    scopus 로고
    • special issue on organocatalysis
    • (c) Acc. Chem. Res. 2004, 37 (8), special issue on organocatalysis.
    • (2004) Acc. Chem. Res , vol.37 , Issue.8
  • 30
    • 51749124913 scopus 로고    scopus 로고
    • special issue on organocatalysis
    • (i) Chem. Rev. 2007, 107 (12), special issue on organocatalysis.
    • (2007) Chem. Rev , vol.107 , Issue.12
  • 33
    • 34250613134 scopus 로고    scopus 로고
    • For general reviews of organocatalytic conjugate addition, see:a
    • For general reviews of organocatalytic conjugate addition, see:(a) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
    • (2007) Eur. J. Org. Chem , pp. 1701
    • Tsogoeva, S.B.1
  • 36
    • 33846550172 scopus 로고    scopus 로고
    • For some recent examples of enamine organocatalyzed reactions, see, for example:a
    • For some recent examples of enamine organocatalyzed reactions, see, for example:(a) Yang, J. W.; Stadler, M.; List, B. Angew. Chem., Int. Ed. 2007, 46, 609.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 609
    • Yang, J.W.1    Stadler, M.2    List, B.3
  • 50
    • 38349100690 scopus 로고    scopus 로고
    • See the following revision in enamine chemistry: o
    • See the following revision in enamine chemistry: (o) Mukherjee, S.; Woon-Yang, J.; Hoffman, S.; List, B. Chem. Rev. 2007, 107, 5471.
    • (2007) Chem. Rev , vol.107 , pp. 5471
    • Mukherjee, S.1    Woon-Yang, J.2    Hoffman, S.3    List, B.4
  • 51
    • 33846957738 scopus 로고    scopus 로고
    • For some recent examples of iminium activation, see, for example, a
    • For some recent examples of iminium activation, see, for example, :(a) Bertelsen, S.; Dinér, P.; Johansen, R. L.; Jørgensen, K. A. J. Am. Chem. Soc. 2007, 129, 1536.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 1536
    • Bertelsen, S.1    Dinér, P.2    Johansen, R.L.3    Jørgensen, K.A.4
  • 61
    • 38349178582 scopus 로고    scopus 로고
    • See the following revision in iminium chemistry: k
    • See the following revision in iminium chemistry: (k) Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416.
    • (2007) Chem. Rev , vol.107 , pp. 5416
    • Erkkilä, A.1    Majander, I.2    Pihko, P.M.3
  • 69
    • 35048898034 scopus 로고    scopus 로고
    • For other revisions about radicals in organocatalysis, see: e
    • For other revisions about radicals in organocatalysis, see: (e) Bertelsen, S.; Nielsen, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 7356.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 7356
    • Bertelsen, S.1    Nielsen, M.2    Jørgensen, K.A.3
  • 71
    • 27544485685 scopus 로고    scopus 로고
    • One example of a TMS-enolate of a tertiary amino lactone adding to an α,β-unsatuarated aldehyde in enantioselective organo-cascade catalysis has been reported:(a) Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
    • One example of a TMS-enolate of a tertiary amino lactone adding to an α,β-unsatuarated aldehyde in enantioselective organo-cascade catalysis has been reported:(a) Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
  • 72
    • 3042799070 scopus 로고    scopus 로고
    • For a review on diversity oriented synthesis, see:a
    • For a review on diversity oriented synthesis, see:(a) Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 46
    • Burke, M.D.1    Schreiber, S.L.2
  • 73
    • 13444267885 scopus 로고    scopus 로고
    • For the first application of diarylprolinol silyl ethers as catalysts, see: a
    • For the first application of diarylprolinol silyl ethers as catalysts, see: (a) Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jørgensen, K. A. Angew. Chem. Int. Ed 2005, 44, 794.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 794
    • Marigo, M.1    Wabnitz, T.C.2    Fielenbach, D.3    Jørgensen, K.A.4
  • 78
    • 51749083968 scopus 로고    scopus 로고
    • 1H NMR spectroscopy of the crude mixture. However during the purification process by flash chromatography the epimerization of the hemi-aminal center was observed (see Supporting Information for more details).
    • 1H NMR spectroscopy of the crude mixture. However during the purification process by flash chromatography the epimerization of the hemi-aminal center was observed (see Supporting Information for more details).
  • 81
    • 51749098236 scopus 로고    scopus 로고
    • CCDC 677671 contains the supplementary crystallographic data. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336-033. E-mail: ].
    • CCDC 677671 contains the supplementary crystallographic data. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336-033. E-mail: ].
  • 92
    • 51749085364 scopus 로고    scopus 로고
    • Frisch, M. J. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh PA, 1998.
    • (a) Frisch, M. J. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh PA, 1998.
  • 93
    • 51749093564 scopus 로고    scopus 로고
    • Frisch, M. J.; Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh PA, 2003.
    • (b) Frisch, M. J.; Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh PA, 2003.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.