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Volumn 8, Issue 16, 2010, Pages 3635-3637

Asymmetric synthesis of proline-based conformationally constrained tryptophan mimetic

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLMETALS; ASYMMETRIC SYNTHESIS; HOMOALLYLIC AMINES; IN-SITU; INDOLE MOIETY;

EID: 77955100690     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00118j     Document Type: Article
Times cited : (16)

References (41)
  • 30
    • 0028915391 scopus 로고
    • Allylzirconocenes typically add to carbonyl compounds in a γ-regioselective manner with predominant anti-stereoselectivity
    • H. Ito T. Nakamura T. Taguchi Y. Hanzawa Tetrahedron 1995 51 4507
    • (1995) Tetrahedron , vol.51 , pp. 4507
    • Ito, H.1    Nakamura, T.2    Taguchi, T.3    Hanzawa, Y.4
  • 34
    • 0002446724 scopus 로고
    • B. M. Trost, I. Fleming, C. W. Heathock, ed.; Pergamon, Oxford
    • The reactions of allylic metals with imines are often capricious, for reviews see: W. Roush, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, C. W. Heathock, ed.; Pergamon, Oxford, 1991; Vol. 2, p. 1.
    • (1991) Comprehensive Organic Synthesis , pp. 1
    • Roush, W.1
  • 35
    • 4243893500 scopus 로고
    • No product was observed when adding benzyloxyacetaldehyde-derived imine 1 to A The predominant syn selectivity was observed in the reaction of imines with allylic zirconocenes also in the absence of additives, see ref. 16
    • Y. Yamamoto N. Asao Chem. Rev. 1993 93 2207
    • (1993) Chem. Rev. , vol.93 , pp. 2207
    • Yamamoto, Y.1    Asao, N.2
  • 39
    • 23944497536 scopus 로고    scopus 로고
    • Compound 1′′rather than 1 was chosen owing to the anticipated incompatibility of Ru-based oxidation conditions with the presence of the Boc-protected indolyl group Improvement in the anti diastereoselectivity was observed for the reactions of allylic zirconocenes with aldehydes, see ref. 14b
    • P. Wipf J. G. Pierce Org. Lett. 2005 7 3537
    • (2005) Org. Lett. , vol.7 , pp. 3537
    • Wipf, P.1    Pierce, J.G.2
  • 40
    • 0001376827 scopus 로고
    • 2 in the presence of Pd/C catalyst led to exclusive N-deprotection; the inhibition of O-debenzylation by nonaromatic amines has been reported
    • S. K. Latypov J. M. Seco E. Quinoà R. Riguera J. Org. Chem. 1995 60 1538
    • (1995) J. Org. Chem. , vol.60 , pp. 1538
    • Latypov, S.K.1    Seco, J.M.2    Quinoà, E.3    Riguera, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.