Formal [2+2] cycloaddition of 2-(acylamino)acrylates with vinyl sulfides: An approach to cyclobutane alpha-amino acids as S-phenylcysteine analogues

Two new types of conformationally restricted S-phenylcysteine are presented. The restriction comprises a cyclobutane unit that includes the alpha- and beta-carbons of the a-amino acid. The synthetic strategy is based on a formal [2+2] cycloaddition between 2-(acylamino)acrylates as acceptor alkenes...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 5; pp. 743 - 746
Main Authors Avenoza, Alberto, Busto, Jesus H., Mata, Lara, Peregrina, Jesus M., Perez-Fernandez, Marta
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.03.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
aldol reaction
ORGANIC-SYNTHESIS
Michael additions
amino acids
cysteine
KETENE DIETHYL ACETAL
cycloadditions
2-ACYLAMINOACRYLATES
aluminum
DERIVATIVES
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Summary:Two new types of conformationally restricted S-phenylcysteine are presented. The restriction comprises a cyclobutane unit that includes the alpha- and beta-carbons of the a-amino acid. The synthetic strategy is based on a formal [2+2] cycloaddition between 2-(acylamino)acrylates as acceptor alkenes and vinyl sulfides as donor alkenes, promoted by aluminum-derived bulky Lewis acids.
ISSN:0039-7881
DOI:10.1055/s-2008-1032171