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Regio- and stereoselective synthesis of isoxazolidine derivatives by asymmetric 1,3-dipolar cycloaddition reaction of chiral nitrones with 1-propene-1,3-sultone

✍ Scribed by Hong-Kui Zhang; Wing-Hong Chan; Albert W. M. Leeb; Wai-Yeung Wong

Publisher: Journal of Heterocyclic Chemistry
Year: 2008
Tongue: English
Weight: 445 KB
Volume: 45
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570450402

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✦ Synopsis

Abstract

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Asymmetric 1,3‐dipolar cycloadditions of chiral nitrones to 1‐propene‐1,3‐sultone (1) were investigated. Chiral nitrones 6a‐e reacted with sultone 1 in toluene at 90 °C for 24‐36 h to give the corresponding isoxazolidines in moderate yields with high regioselectivities and stereoselectivities. The diastereoselectivity of this reaction varied with the choice of dipolarophile and the steric demands of nitrones. When sultone 1 was allowed to react chiral nitrone 6e, a much better diastereoselectivity of up to 5.1:1 was observed.

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