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