3-Acyl-2-( N-cyanoimino)oxazolidine derivative, a new asymmetric acylating agent for racemic secondary alkyl amines

A 3-acyl-2-( N-cyanoimino)oxazolidine derivative was found to serve as an enantioselective acylating agent for sec-alkyl amines. These reagents differentiate the enantiomers of 1-phenylethylamine derivatives up to 85% ee, and the recovered chiral auxiliary is reusable. Graphic

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Bibliographic Details
Published inTetrahedron Vol. 57; no. 45; pp. 9309 - 9315
Main Authors Maezaki, Naoyoshi, Furusawa, Akemi, Uchida, Shuji, Tanaka, Tetsuaki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.11.2001
Elsevier
Subjects
acylation
amines
asymmetric reactions
Chemistry
Chemistry, Organic
Physical Sciences
resolution
Science & Technology
amines
asymmetric reactions
resolution
acylation
ENZYMATIC RESOLUTION
N-N BOND
CHIRAL AXIS
ALCOHOLS
ORGANIC-SOLVENTS
KINETIC RESOLUTION
ENANTIOSELECTIVE ACYLATION
ANHYDRIDE
CHLORIDE
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Summary:A 3-acyl-2-( N-cyanoimino)oxazolidine derivative was found to serve as an enantioselective acylating agent for sec-alkyl amines. These reagents differentiate the enantiomers of 1-phenylethylamine derivatives up to 85% ee, and the recovered chiral auxiliary is reusable. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00933-4