http://dx.doi.org/10.1002/jhet.5570450402">
 

Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

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

Language

English

Abstract

(Chemical Equation Presented) 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.

Publication Date

2009

Source Publication Title

Journal of Heterocyclic Chemistry

Volume

45

Issue

4

Start Page

957

End Page

962

Publisher

Wiley

ISSN (print)

0022152X

ISSN (electronic)

19435193

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