Stereoselective synthesis of iso-dolaproine via dynamic kinetic resolution

D Lavergne; C Mordant; V Ratovelomanana-Vidal; J P Genet

doi:10.1021/ol015955g

Stereoselective synthesis of iso-dolaproine via dynamic kinetic resolution

Org Lett. 2001 Jun 14;3(12):1909-12. doi: 10.1021/ol015955g.

Authors

D Lavergne¹, C Mordant, V Ratovelomanana-Vidal, J P Genet

Affiliation

¹ Laboratoire 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.

PMID: 11405742
DOI: 10.1021/ol015955g

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis*
Amino Acids / chemistry
Catalysis
Kinetics
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Stereoisomerism

Substances

Amino Acids
Pyrrolidines
dolaproine