Synlett 2007(20): 3198-3200  
DOI: 10.1055/s-2007-992376
LETTER
© Georg Thieme Verlag Stuttgart · New York

Dimethyldioxirane Oxidation of 2-Silyloxypyrroles: An Efficient Regiocontrolled Synthesis of 5-Hydroxy-3-pyrrolin-2-ones

John Boukouvalas*, Yufang Xiao, Yun-Xing Cheng, Richard P. Loach
Département de Chimie, Université Laval, Quebec City, QC, G1K 7P4, Canada
Fax: +1(418)6567916; e-Mail: john.boukouvalas@chm.ulaval.ca;
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Publikationsverlauf

Received 16 August 2007
Publikationsdatum:
21. November 2007 (online)

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Abstract

A new method for the synthesis of 5-hydroxy-3-pyrrolin-2-ones is reported. Conversion of N-Boc-3-pyrrolin-2-ones into 2-triisopropylsilyloxypyrroles and ensuing oxidation with dimethyldioxirane provides the corresponding N-Boc-5-hydroxy-3-pyrrolin-2-ones in high yields.