title: Stereoselective synthesis of iso-dolaproine via dynamic kinetic resolution.
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.
authors.affiliation: 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.
authors.forename: D
authors.initials: D
authors.lastname: Lavergne
authors.forename: C
authors.initials: C
authors.lastname: Mordant
authors.forename: V
authors.initials: V
authors.lastname: Ratovelomanana-Vidal
authors.forename: J P
authors.initials: JP
authors.lastname: Genet
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007700:Kinetics; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D011759:Pyrrolidines; C098461:dolaproine