ERYTHRO-SELECTIVE ALDOL-TYPE REACTION OF N-SULFONYLALDIMINES WITH METHYL ISOCYANOACETATE CATALYZED BY GOLD(I)

Authors
HAYASHI T KISHI E SOLOSHONOK VA UOZUMI Y
Citation
T. Hayashi et al., ERYTHRO-SELECTIVE ALDOL-TYPE REACTION OF N-SULFONYLALDIMINES WITH METHYL ISOCYANOACETATE CATALYZED BY GOLD(I), Tetrahedron letters, 37(28), 1996, pp. 4969-4972
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
28
Year of publication
1996
Pages
4969 - 4972
Database
ISI
SICI code
0040-4039(1996)37:28<4969:EARONW>2.0.ZU;2-T
Abstract
Reaction of N-tosylaldimines 1 with methyl isocyanoacetate in the pres ence of 1 mol % of AuCl(c-HexNC) gave 4-methoxycarbonyl-5-alkyl-2-imid azolines 2 with high (over 89 %) cis selectivity. The cis-imidazolinec arboxylates were isomerized into trans isomers by treatment with triet hylamine. Hydrolysis of the cis- and trans-imidazolinecarboxylates gav e erythro- and threo-alpha,beta-diamino acids, respectively. Copyright (C) 1996 Elsevier Science Ltd