Asymmetric hydrogenation reactions mediated by a new class of bicyclic bisphosphinites

被引：23

作者：

Derrien, N

Dousson, CB

Roberts, SM

Berens, U

Burk, MJ

Ohff, M

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

[2] Chirotech Technol Ltd, Cambridge CB4 4WE, England

[3] Univ Rostock EV, Inst Organ Katalyseforsch, D-18055 Rostock, Germany

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(99)00341-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The bicyclic alcohol (-)-4 was prepared from (-)-bicyclo[3.2.0]hept-2-en-6-one (-)-1 in 50% yield. The diol (-)-4 was coupled to selected chlorophosphines 6-12 to produce a series of bisphosphinites 13-19 in 89-95% yield. From these bisphosphinites were prepared the rhodium complexes 20-26 which were characterised by P-31 NMR and used in situ for the asymmetric hydrogenation of alpha-enamides 27-29. Complexes 21, 23-25 proved to be the superior catalysts for the production of (R)-N-acetylphenylalanine (91, 84, 90 and 87.5% ee) from 27 and (S)-N-acetylalanine methyl ester (70, 72, 68 and 71% ee) from 28. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3341 / 3352

页数：12