SYNTHESIS OF BETA-FUNCTIONALIZED ALPHA,BETA-DEHYDROAMINO ACID-DERIVATIVES

.beta.-Functionalized .alpha.,.beta.-unsaturated amino acids were synthesized by an addition-elimination pathway. Reaction of methyl .beta.-bromo-.alpha.-formylaminoacrylates (3a-e), which were prepared by the condensation of methyl isocyanoacetate (1) with aldehydes followed by bromination, with th...

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Bibliographic Details
Published inTetrahedron Vol. 44; no. 17; pp. 5467 - 5478
Main Authors NUNAMI, K, HIRAMATSU, K, HAYASHI, K, MATSUMOTO, K
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.1988
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:.beta.-Functionalized .alpha.,.beta.-unsaturated amino acids were synthesized by an addition-elimination pathway. Reaction of methyl .beta.-bromo-.alpha.-formylaminoacrylates (3a-e), which were prepared by the condensation of methyl isocyanoacetate (1) with aldehydes followed by bromination, with thiols gave .beta.-alkylthio-.alpha.,.beta.-unsaturated amino acid derivatives (6a-f). The reaction of (3a) with sodium azide resulted in the formation of a 2-oxoimidazoline derivative (4). On the other hand, .beta.-benzyloxy- and .beta.-benzylamino-.alpha.-.beta.-unsaturated amino acids (9 and 12) were synthesized by the reaction of methyl .beta.-bromo-.alpha.-isocyanocinnamates (7a and 7d), prepared from (3a and 3d), with benzyl alcohol and benzylamine followed by acidic hydration, respectively.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)86052-X