Asymmetric syntheses .26. Catalytic enantioselective syntheses of beta-hydroxy esters via double chiral induction in asymmetric Reformatsky reactions

被引：15

作者：

Mi, AQ ^{[1
]}

Wang, ZY ^{[1
]}

Zhang, JM ^{[1
]}

Jiang, YZ ^{[1
]}

机构：

[1] CHINESE ACAD SCI,UNION LAB ASYMMETR SYNTHESIS,CHENGDU INST ORGAN CHEM,CHENGDU 610041,PEOPLES R CHINA

来源：

SYNTHETIC COMMUNICATIONS | 1997年 / 27卷 / 09期

关键词：

D O I：

10.1080/00397919708006081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric Reformatsky reactions of benzaldehyde with optically active menthyl bromoacetates in the presence of Zn-Cu couple were performed using 0.25 equiv. of (1R,2S) or (1S,2R)-N,N-dimethyl-2-amino-1,2-diphenyl ethanol as chiral ligand to obtain beta- hydroxy esters with enantioselectivities up to 60.2%. The obvious double chiral induction effect was observed while chiral ligands matched with optically active substrates.

引用

页码：1469 / 1473

页数：5

共 9 条

[1]

COHEN SG, 1964, J AM CHEM SOC, V86, P726

[2]

JIANG YZ, 11 INT C ORG SYNTH I

[3]

JIANG YZ, 1994, YOUJI HUAXUE, V14, P68

[4] Walden inversion reactions of the p-toluenesulphinic and the p-toluenesuphonic esters of ethyl d-beta-hydroxy-beta-phenylpropionate. [J].