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

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.

SUBMITTER: Williams DR

PROVIDER: S-EPMC3566646 | biostudies-literature | 2010 Feb

REPOSITORIES: biostudies-literature

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

Williams David R DR Fu Liangfeng L

Organic letters 20100201 4

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. ...[more]

PMID: 20085311

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