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Paper | Regular issue | Vol 78, No. 12, 2009, pp.3053-3064
Published online, 2nd October, 2009
DOI: 10.3987/COM-09-11826
Efficient Synthesis of 4-Substituted 4,5-Dihydroisoxazol-3-ols from Morita-Baylis-Hillman Bromides

Weihui Zhong,* Yongliang Liu, and Baoming Guo

*Key Laboratory of Pharmaceutical Engineering of Ministry of Educations, College of Pharmaceutical Sciences, Zhejiang University , Hangzhou 310014, China

Abstract

An efficient synthesis of 4-substituted 4,5-dihydroisoxazol-3-ols was achieved with high regioselectivities and satisfactory yields via addition of N-hydroxyphthalimide to Morita-Baylis-Hillman (MBH) bromides with ester moiety, followed by hydrazinolysis and intramolecular cyclization. Surprised, the unexpected isoxazolidine-4-carbonitrile was obtained when using MBH bromide with nitrile moiety as substrate under the similar conditions.