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Stereoselective synthesis of iso-dolaproine via dynamic kinetic resolution
D Lavergne1, C Mordant, V Ratovelomanana-Vidal
1Laboratoire de Synthèse Sélective Organique et Produits Naturels, UMR 7573 C.N.R.S., Ecole Nationale Supérieure de Chimie de Paris, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France.
Organic Letters
|June 19, 2001
Abstract:
[see reaction]. An efficient multigram-scale synthesis of optically pure Boc-(2S,3R,4S)-iso-dolaproine is reported using dynamic kinetic resolution (DKR). The catalytic asymmetric hydrogenation of ethyl (4S)-3-(2'-pyrrolidinyl)-3-oxo-2-methyl propanoate hydrochloride using in situ generated Ru[(S)-MeO-BIPHEP]Br2 catalyst affords the anti beta-hydroxy alpha-methyl ester quantitatively. The two new stereogenic centers are simultaneously controlled with high diastereoselectivity.