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General Methodology for the Preparation of 2,5-disubstituted-1,3-oxazoles

David R Williams, Liangfeng Fu

Org Lett. 2010 Feb 19;12(4):808-11.

PMID: 20085311

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP145214057 2-(Tri-n-butylstannyl)oxazole 2-(Tri-n-butylstannyl)oxazole 145214-05-7 Price
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