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Volumn 53, Issue 19, 1997, Pages 6611-6634

Solid phase synthesis of fused bicyclic amino acid derivatives via intramolecular Pauson-Khand cyclization: Versatile scaffolds for combinatorial chemistry

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE;

EID: 0030987008     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00220-2     Document Type: Conference Paper
Times cited : (79)

References (45)
  • 14
    • 0001334715 scopus 로고
    • Trost, B. M., Ed.; Pergamon: Oxford
    • For recent reviews, see: a) Schore, N. E. in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p. 1037.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1037
    • Schore, N.E.1
  • 30
    • 0029978630 scopus 로고    scopus 로고
    • For a preliminary account of a portion of this work, see: Bolton, G.L. Tetrahedron Lett. 1996, 37, 3433-3436.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3433-3436
    • Bolton, G.L.1
  • 31
    • 84920294310 scopus 로고    scopus 로고
    • note
    • The coupling constant of 7 Hz for the C-3 methine proton appearing as a doublet at 5.11 ppm is indicative of an axial carbomethoxy group at this position, assuming a chair conformation for the piperidine ring. The protons for C-l appearing at 2.51 (dd, J=19 and 6Hz) and 1.92 (dd, J=19 and 2Hz) support an axial bridgehead proton at C-7a.
  • 32
    • 84920294309 scopus 로고    scopus 로고
    • note
    • The authors have deposited the atomic coordinates for 6, 10, and 36 with the Cambridge Crystallographic Data Centre. Additional experimental details are provided as supplementary material.
  • 42
    • 84920294308 scopus 로고    scopus 로고
    • note
    • The protons at C-1 appearing at 3.76 (d, J=13Hz) and 3.48 (dd, J=13 and 3Hz) are indicative of an equatorial proton at C-7a, assuming a chair conformation for the piperidine ring.
  • 44
    • 84955066834 scopus 로고
    • b) For another example of reductive amination of a resin-bound ketone substrate, see: Ley, S.V.; Mynett, D.M.; Koot, W.-J. Synlett 1995, 1017-1020.
    • (1995) Synlett , pp. 1017-1020
    • Ley, S.V.1    Mynett, D.M.2    Koot, W.-J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.