NEW ROUTES TO α-AMINO ACID β,γ-THIOENOL ETHER DERIVATIVES

Racemic derivatives of α-amino acid β,γ-thioenol ethers have been synthesized from homoserine through a γ-elimination on a sulfoxide derived from aspartaldehyde. Optically active derivatives were efficiently prepared from L-methionine by a Pummerer like reaction.

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Bibliographic Details
Published inSynthetic communications Vol. 32; no. 2; pp. 287 - 296
Main Authors Meffre, Patrick, Durand, Philippe
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.01.2002
Marcel Dekker Inc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
METHIONINE ANALOG
S-ADENOSYLMETHIONINE
L-2-AMINO-4-METHOXY-CIS-BUT-3-ENOIC ACID
CARBON DOUBLE-BONDS
METHYL (S)-2-PHTHALIMIDO-4-OXOBUTANOATE
SUBSTITUENTS
STABILITIES
L-2-AMINO-4-METHOXY-TRANS-BUT-3-ENOIC ACID
ENZYME INACTIVATORS
INHIBITOR
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Summary:Racemic derivatives of α-amino acid β,γ-thioenol ethers have been synthesized from homoserine through a γ-elimination on a sulfoxide derived from aspartaldehyde. Optically active derivatives were efficiently prepared from L-methionine by a Pummerer like reaction.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-120002014