Journal Articles Journal of Organic Chemistry Year : 2010

Synthesis of 2-Trifluoromethyl-1,3-oxazolidines as Hydrolytically Stable Pseudoprolines

Abstract

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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hal-02310997 , version 1 (10-10-2019)

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Grégory Chaume, Olivier Barbeau, Philippe Lesot, Thierry Brigaud. Synthesis of 2-Trifluoromethyl-1,3-oxazolidines as Hydrolytically Stable Pseudoprolines. Journal of Organic Chemistry, 2010, 75 (12), pp.4135-4145. ⟨10.1021/jo100518t⟩. ⟨hal-02310997⟩
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