메뉴 건너뛰기




Volumn 37, Issue 25, 1996, Pages 4309-4312

Synthesis of higher α-chlorovinyl and α-bromovinyl amino acids: The amino protecting group determines the reaction course

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALPHA AMINO ACID; BROMIDE; CHLORIDE; ESTER; VINYL DERIVATIVE;

EID: 0029882654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00832-5     Document Type: Article
Times cited : (14)

References (34)
  • 13
    • 85030208632 scopus 로고    scopus 로고
    • note
    • We define higher α-halovinyl amino acids as α-amino acids bearing the usual α-side chain (≠H) and an additional halovinyl substituent in place of the usual α-proton.
  • 14
    • 85030207602 scopus 로고    scopus 로고
    • note
    • To our knowledge, there is only one previously reported synthesis of a higher α-halovinyl amino acid. Namely, treatment of 3,4-dimethoxy-α-ethynylphenylalanine with 47% HBr at reflux for 4 h yields internal α-bromovinyl-DOPA in 31% yield: reference 8j.
  • 15
    • 0027445840 scopus 로고
    • For other synthetic approaches to higher α-vinyl amino acids, see: (a) Colson, P.-J.; Hegedus., L. S. J. Org. Chem. 1993, 58, 5918-5924;
    • (1993) J. Org. Chem. , vol.58 , pp. 5918-5924
    • Colson, P.-J.1    Hegedus, L.S.2
  • 28
    • 0001537818 scopus 로고
    • For earlier pioneering work on related applications of PhSeX reagents, see: (a) Sharpless, K. B.; Lauer, R. F. J. Org. Chem. 1974, 39, 429-430;
    • (1974) J. Org. Chem. , vol.39 , pp. 429-430
    • Sharpless, K.B.1    Lauer, R.F.2
  • 32
    • 85030206130 scopus 로고    scopus 로고
    • note
    • + 308.1287, obsd 308.1278.
  • 34
    • 85030205675 scopus 로고    scopus 로고
    • note
    • + 324.1236, obsd 324.1239.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.