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. 2010 Feb 19;12(4):808-11.
doi: 10.1021/ol902833p.

General methodology for the preparation of 2,5-disubstituted-1,3-oxazoles

David R Williams  1 , Liangfeng Fu
Affiliations

General methodology for the preparation of 2,5-disubstituted-1,3-oxazoles

David R Williams et al. Org Lett. .

Abstract

Deprotonation of 2-(phenylsulfonyl)-1,3-oxazole (1) readily provides a useful C-5 carbanion that is reactive with a variety of electrophiles. Aldehydes and ketones are useful substrates, and the formation of 5-iodo- and 5-tri-n-butylstannyl oxazoles affords access to cross-coupling reactions. Subsequent nucleophilic displacement of the 2-phenylsulfonyl group provides a general route for the synthesis of 2,5-disubstituted-1,3-oxazoles.

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Figures

Scheme 1
Scheme 1
Site Selective Substitutions of 1,3-Oxazole
Scheme 2
Scheme 2
Selective C-4 Deprotonation of Imidaxzole 4
Scheme 3
Scheme 3
Negishi Coupling for C-5 Allylation of 1
Scheme 4
Scheme 4
Stille Cross Coupling Reactions
See this image and copyright information in PMC

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