Synthesis of both syn and anti diastereoisomers of Boc-dolaproine from (S)-proline through DKR using ruthenium-catalyzed hydrogenation:: a dramatic role of N-protecting groups

被引：23

作者：

Mordant, C ^{[1
]}

Reymond, S ^{[1
]}

Ratovelomanana-Vidal, V ^{[1
]}

Genêt, JP ^{[1
]}

机构：

[1] ENSCP, Lab Synth Select Organ & Prod Nat, UMR 7573, F-75231 Paris 05, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 43期

关键词：

dolaproine; DKR; asymmetric hydrogenation; ruthenium;

D O I：

10.1016/j.tet.2004.07.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The natural (2R,3R)-Boc-dolaproine and its unnatural (2S,3S) diastereoisomer were synthesized involving as key transformation the Ru(II)-promoted hydrogenation of the beta-keto-alpha-methyl ester derived from (S)-N-Boc-proline. Interestingly, the asymmetric hydrogenation of this beta-keto ester N-protected as an amine hydrochloride salt, provided the corresponding anti (2S,3R)- and (2R,3S)-beta-hydroxy-alpha-methyl esters with significant level of selectivities through dynamic kinetic resolution. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：9715 / 9723

页数：9