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Letter

Straightforward Synthesis of (S)- and (R)-α-Trifluoromethyl Proline from Chiral Oxazolidines Derived from Ethyl Trifluoropyruvate

Supporting Info

Grégory Chaume, Marie-Céline Van Severen, Sinisa Marinkovic, and Thierry Brigaud*

Laboratoire Synthse Organique Slective et Chimie Organomtallique (SOSCO), UMR CNRS 8123, Universit de Cergy-Pontoise, 5, Mail Gay-Lussac-Neuville sur Oise 95031, Cergy-Pontoise Cedex, France

Org. Lett., 2006, 8 (26), pp 6123–6126

DOI: 10.1021/ol062593+

Publication Date (Web): November 30, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, thierry.brigaud@u-cergy.fr

Abstract

A concise synthesis of both enantiomers of α-Tfm-proline and (S)-α-Tfm-prolinol from ethyl trifluoropyruvate is reported. The key step is a diastereoselective allylation reaction of ethyl trifluoropyruvate and (R)-phenylglycinol-based oxazolidines or imine. The lactone obtained by cyclization of the resulting hydroxy ester proved to be a valuable intermediate for the synthesis of (S)-α-Tfm-allylglycine and (S)-α-Tfm-norvaline in enantiopure form.

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Published In Issue December 21, 2006
Received October 21, 2006

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Letter

Straightforward Synthesis of (S)- and (R)-α-Trifluoromethyl Proline from Chiral Oxazolidines Derived from Ethyl Trifluoropyruvate