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Volumn , Issue 21, 2009, Pages 3611-3616

A short and convenient synthesis of enantiopure cis- And trans-4-hydroxypipecolic acid

Author keywords

Amino acids; Carbonylations; Coupling; Lactams; Palladium

Indexed keywords

ACID PRODUCTS; CARBONYLATIONS; CONJUGATE ADDITION; DOUBLE BONDS; ENAMINES; ENANTIOPURE; LACTAMS; METHOXYCARBONYLATION; STEREOSELECTIVE HYDROGENATION; UNSATURATED ESTERS;

EID: 72049095604     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216979     Document Type: Article
Times cited : (21)

References (51)
  • 19
    • 23944496414 scopus 로고    scopus 로고
    • For a recent review on the asymmetric synthesis of pipecolic acids and derivatives see: (a) Kadouri-Puchot, C.; Comesse, S. Amino Acids 2005, 29, 101.
    • (2005) Amino Acids , vol.29 , pp. 101
    • Kadouri-Puchot, C.1    Comesse, S.2
  • 36
    • 72049103067 scopus 로고    scopus 로고
    • Purification is not necessary, but a much cleaner lactam is obtained if the protected nitrile is purified by chromatography
    • Purification is not necessary, but a much cleaner lactam is obtained if the protected nitrile is purified by chromatography.
  • 38
  • 41
    • 72049086338 scopus 로고    scopus 로고
    • Elimination of ROH to give an α,β,γ,δ-unsaturated ester has been sometime observed by us in the presence of acids, even when compound 10 was stored in fridge and traces of acids were present. The same elimination occurs with phosphate 9
    • Elimination of ROH to give an α,β,γ,δ-unsaturated ester has been sometime observed by us in the presence of acids, even when compound 10 was stored in fridge and traces of acids were present. The same elimination occurs with phosphate 9.
  • 46
    • 72049111176 scopus 로고    scopus 로고
    • 3): δ = 4.97 (m, 1 H), 4.90-4.70 (br m, 1 H), 4.30-4.00 (br m, 1 H), 3.74 (s, 3 H), 3.35-3.15 (br m, 1 H), 2.55-2.40 (m, 1 H), 2.40-2.37 (m, 1 H), 2.14-2.05 (m, 1 H), 1.98-1.85 (m, 1 H)
    • 3): δ = 4.97 (m, 1 H), 4.90-4.70 (br m, 1 H), 4.30-4.00 (br m, 1 H), 3.74 (s, 3 H), 3.35-3.15 (br m, 1 H), 2.55-2.40 (m, 1 H), 2.40-2.37 (m, 1 H), 2.14-2.05 (m, 1 H), 1.98-1.85 (m, 1 H).
  • 47
    • 0025730945 scopus 로고
    • axial. Enantiopure cis-isomer (2S,4R)-13 has been already prepared by us (see ref. 13) and, in its racemic form, by Hiemstra and Speckamp. See: (a) Esch, P. M.; de Boer, R. F.; Hiemstra, H.; Boska, I. M.; Speckamp, W. N. Tetrahedron 1991, 47, 4063.
    • (1991) Tetrahedron , vol.47 , pp. 4063
    • Esch, P.M.1    De Boer, R.F.2    Hiemstra, H.3    Boska, I.M.4    Speckamp, W.N.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.