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A Direct Synthesis of Oxazoles from Aldehydes

Thomas H. Graham*

*Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065-0900, Email: thomas.grahammerck.com

T. H. Graham, Org. Lett., 2010, 12, 3614-3617.

DOI: 10.1021/ol101346w (free Supporting Information)


Abstract

An expedient and mild method for the direct conversion of aldehydes to 2,4-disubstituted oxazoles relies on the oxidation of an oxazolidine formed from the condensation of serine with an aldehyde and proceeds through a 2,5-dihydrooxazole intermediate. In contrast to standard methods that start from carboxylic acids, the use of aldehydes as starting materials does not require intermediate purification.

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Key Words

Oxazoles


ID: J54-Y2010-2260