Synthesis of 2-trifluoromethyl-1,3-oxazolidines as hydrolytically stable pseudoprolines.

J Org Chem

Laboratoire SOSCO, Université de Cergy-Pontoise, 5 Mail Gay-Lussac, Neuville sur Oise, 95000 Cergy-Pontoise cedex, France.

Published: June 2010

Trifluoromethyl group containing oxazolidines (Fox) are conveniently synthesized by condensation of serine esters with trifluoroacetaldehyde hemiacetal or trifluoroacetone. These oxazolidines can undergo N-acylation and amidification reactions and are completely configurationally and hydrolytically stable. Therefore, they can be considered as highly valuable proline surrogates (Tfm-pseudoprolines).

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Source
http://dx.doi.org/10.1021/jo100518tDOI Listing

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