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Volumn , Issue 11, 2004, Pages 2359-2366

Lewis acid-mediated diastereoselective reduction of N-protected β-amino ketones: Influence of the nature of the metal atom and of the nitrogen protecting group

Author keywords

Amino alcohols; Chelates; Lewis acids; Protecting groups; Reduction

Indexed keywords

LEWIS ACID; LITHIUM BOROHYDRIDE; LITHIUM DERIVATIVE; NITROGEN; SOLVENT; UNCLASSIFIED DRUG;

EID: 4544238015     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400016     Document Type: Article
Times cited : (13)

References (93)
  • 8
    • 0001222924 scopus 로고
    • [2e] S. Knapp, Chem. Rev. 1995, 95, 1859-1876.
    • (1995) Chem. Rev. , vol.95 , pp. 1859-1876
    • Knapp, S.1
  • 44
    • 0000964801 scopus 로고
    • (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford
    • [11b] S. Shambayati, S. L. Schreiber, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, vol. 1, pp. 283-324.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 283-324
    • Shambayati, S.1    Schreiber, S.L.2
  • 48
    • 4544251067 scopus 로고    scopus 로고
    • note
    • Racemic substrates are used. For the sake of simplicity, only one enantiomer is shown in schemes and tables.
  • 72
    • 0003872342 scopus 로고
    • (Ed.: M. Schlosser), John Wiley & Sons, Chichester
    • [27e] M. T. Reetz, in Organometallics in Synthesis (Ed.: M. Schlosser), John Wiley & Sons, Chichester, 1994, pp. 195-282.
    • (1994) Organometallics in Synthesis , pp. 195-282
    • Reetz, M.T.1
  • 82
    • 0030012561 scopus 로고    scopus 로고
    • 3 prepared by the Imamoto procedure (see N. Takeda, T. Imamoto, Org. Synth. 1998, 76, 228-235); however, the material was highly efficient without the need for a large excess of reducing agent.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4581-4584
    • Evans, W.J.1    Feldman, J.D.2    Ziller, J.W.3
  • 83
    • 85028011249 scopus 로고    scopus 로고
    • 3 prepared by the Imamoto procedure (see N. Takeda, T. Imamoto, Org. Synth. 1998, 76, 228-235); however, the material was highly efficient without the need for a large excess of reducing agent.
    • (1998) Org. Synth. , vol.76 , pp. 228-235
    • Takeda, N.1    Imamoto, T.2
  • 85
    • 4544321559 scopus 로고
    • 4 is the reducing agent of choice. This is obtainable from Aldrich or easily prepared according to: H. V. Brown, Y. M. Choi, S. Narasinihau, Inorg. Chem. 1981, 20, 4456-4459.
    • (1981) Inorg. Chem. , vol.20 , pp. 4456-4459
    • Brown, H.V.1    Choi, Y.M.2    Narasinihau, S.3
  • 89
    • 0028892492 scopus 로고
    • Examples of syn- and anti-diastereomers possessing nearly identical coupling constants are known in the literature: R R. Carlier, K. M. Lo, M. M.-C. Lo, I. D. Williams, J. Org. Chem. 1995, 60, 7511-7517.
    • (1995) J. Org. Chem. , vol.60 , pp. 7511-7517
    • Carlier, R.R.1    Lo, K.M.2    Lo, M.M.-C.3    Williams, I.D.4
  • 92
    • 4544249043 scopus 로고    scopus 로고
    • note
    • The RS,SR descriptors indicate that diastereomeric compounds are obtained as racemates. We prefer this terminology to avoid the ambiguities that could arise from syn-anti descriptors.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.