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Volumn , Issue 32, 2011, Pages 6544-6552

Diastereodivergent synthesis of 4-hydroxy-2,3-methanopipecolic acid derivatives as conformationally constrained homoserine analogues

Author keywords

Amino acids; Cyclopropanation; Kinetic resolution; Medicinal chemistry; Nitrogen heterocycles; Nonnatural amino acids

Indexed keywords


EID: 80155125078     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100962     Document Type: Article
Times cited : (16)

References (48)
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    • 42449131742 scopus 로고    scopus 로고
    • L. Isakovic, M. O. Saavedra, D. B. Llewellyn, S. Claridge, L. Zhan, N. Bernstein, A. Vaisburg, D. Delorme, A. Wahhab, N. Elowe, A. J. Petschner, J. Rahil, N. Beaulieu, F. Gauthier, A. R. MacLeod, J. M. Besterman, Bioorg. Med. Chem. Lett. 2009, 19, 2742 (homocysteine). For the synthesis of constrained analogues of homoserine, see for example: K. Undheim, Amino Acids 2008, 34, 357.
    • (2008) Amino Acids , vol.34 , pp. 357
    • Undheim, K.1
  • 39
    • 0000458209 scopus 로고
    • J. Cossy, N. Furet, S. BouzBouz, Tetrahedron 1995, 43, 11751. For a review on substrate-directable chemical reactions including cyclopropanation reactions, see.
    • J. Cossy, N. Furet, S. BouzBouz, Tetrahedron 1995, 43, 11751. For a review on substrate-directable chemical reactions including cyclopropanation reactions, see:, A. H. Hoveyda, D. A. Evans, G. C. Fu, Chem. Rev. 1993, 93, 1307.
    • (1993) Chem. Rev. , vol.93 , pp. 1307
    • Hoveyda, A.H.1    Evans, D.A.2    Fu, G.C.3
  • 47
    • 0004251210 scopus 로고    scopus 로고
    • 1H NMR spectra of compounds 12, 14, and 16 are quite complex due to the presence of rotamers for both trans and cis isomers in solution. However, at least one set of signals allow for the identification of the two isomers and the determination of the ratio, i.e. the 3-H axial proton, which is always 0.4-0.5 ppm more downfield-shifted in the trans isomer. Moreover, 5-H is always a broad singlet due to the lack of trans diaxial coupling.
    • (1996) Advances in Nitrogen Heterocycles
    • Comins, D.L.1    Joseph, S.P.2    Moody, C.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.