PREPARATION OF ACYCLIC N-ACYL-N,O-ACETALS BY DECARBOXYLATION OF N-PROTECTED ALPHA-AMINO-ACIDS AND STUDIES OF ASYMMETRIC AMIDOALKYLATION WITH TRIMETHYLSILYL CYANIDE

Oxidative decarboxylation of N-acyl-alpha-amino acids with lead tetra-acetate followed by treatment with methanol provides a facile method for preparation of acyclic N-acyl-N,O-acetals, which can be used in asymmetric alpha-amidoalkylation reactions using trimethylsilyl cyanide as nucleophile.

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Bibliographic Details
Published inSynthetic communications Vol. 21; no. 12-13; pp. 1409 - 1417
Main Authors HARDING, KE, LIU, LT, FARRAR, DG, COLEMAN, MT, TANSEY, SK
Format Journal Article
LanguageEnglish
Published NEW YORK Marcel Dekker Inc 01.06.1991
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
CARBON
STEREOSELECTION
AMINOCARBOXYLIC ACIDS
DERIVATIVES
THREONINE
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Summary:Oxidative decarboxylation of N-acyl-alpha-amino acids with lead tetra-acetate followed by treatment with methanol provides a facile method for preparation of acyclic N-acyl-N,O-acetals, which can be used in asymmetric alpha-amidoalkylation reactions using trimethylsilyl cyanide as nucleophile.
ISSN:0039-7911
DOI:10.1080/00397919108021290