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Synthesis 2005(15): 2578-2582
DOI: 10.1055/s-2005-872101
DOI: 10.1055/s-2005-872101
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (5R)-4-Methyl-5-phenyl-1,3,4-oxadiazinan-2-one and Some N-Acyl Derivatives from (R)-Phenylglycine
Further Information
Publication History
Received
30 March 2005
Publication Date:
25 July 2005 (online)


Abstract
(5R)-4-Methyl-5-phenyl-1,3,4-oxadiazinan-2-one was synthesized from (R)-phenylglycine in five steps and in 65% overall yield. In addition, a convenient and practical method for N-acylation of 1,3,4-oxadiazinan-2-one directly with acids in the presence of DCC and catalytic quantities of DMAP is described. The acylated products were obtained in excellent yields.
Key words
(R)-phenylglycine - 1,3,4-oxadiazinan-2-ones - heterocycles - acylation - carboxylic acids