PHOSPHINITES OF CARBOHYDRATES AS CHIRAL LIGANDS FOR ASYMMETRIC-SYNTHESIS CATALYZED BY COMPLEXES .2. SUPERIORITY OF PHENYL 4,6-O-(R)-BENZYLIDENE-2,3-O-BIS(DIPHENYLPHOSPHINO)-BETA-D-GLUCOPYRANOSIDE FOR RHODIUM(I)-CATALYZED HYDROGENATION OF AMINO-ACID PRECURSORS

被引:117
作者
SELKE, R
PRACEJUS, H
机构
[1] Acad of Sciences of GDR, Rostock, East Ger, Acad of Sciences of GDR, Rostock, East Ger
来源
JOURNAL OF MOLECULAR CATALYSIS | 1986年 / 37卷 / 2-3期
关键词
AMINO ACIDS - Hydrogenation - CATALYSIS - SOLVENTS;
D O I
10.1016/0304-5102(86)85010-6
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Phenyl 4,6-O-(R)-benzylidene-2,3-O-bis(diphenylphosphino) - beta (Ph- beta -glup) 4a, a new air-stable chiral bidenate ligand, is easily prepared from glucose. Its cationic rhodium(I) chelate 5a is useful as a stable and highly active catalyst for asymmetric hydrogenation of N-acyl-dehydro- alpha -amino acids yielding, in 94-99% e. e. , N-acyl-(S)- alpha -amino acids. Only slightly lower e. e. s are obtained for the corresponding esters. The rate of hydrogenation considerably increases with hydrogen pressure, this having practically no influence on the optical yield.
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页码:213 / 225
页数:13
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