HIGHLY ENANTIOSELECTIVE SYNTHESIS OF BETA-HYDROXY NITRILES BY THE CYANOMETHYLATION OF ALDEHYDES USING DPMPM AS A CHIRAL CATALYST OR LIGAND

被引：39

作者：

SOAI, K

HIROSE, Y

SAKATA, S

机构：

[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Shinjuku, Tokyo

来源：

TETRAHEDRON-ASYMMETRY | 1992年 / 3卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(00)80498-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Optically active beta-hydroxy nitriles in up to 93% e.e. were obtained by the enantioselective addition of cyanomethylzinc bromide to aldehydes using DPMPM as a chiral catalyst or ligand.

引用

页码：677 / 680

页数：4

共 20 条

[1]

Bosnich B., 1986, ASYMMETRIC CATALYSIS

[2]

BOSNICH B, 1985, ASYMMETRIC SYNTHESIS, V5

[3]

GOASDOUE N, 1969, CR ACAD SCI C CHIM, V269, P861

[4] ASYMMETRICAL SYNTHESIS OF BETA-HYDROXY ESTERS BY REFORMATSKY REACTION IN PRESENCE OF (-) SPARTEINE [J].

GUETTE, M ;

CAPILLON, J ;

GUETTE, JP .

TETRAHEDRON, 1973, 29 (22) :3659-3667

[5]

HUBSCHER J, 1990, HELV CHIM ACTA, V73, P1068, DOI 10.1002/hlca.19900730431

[6] ENHANCED ENANTIOSELECTIVITY OF AN ENZYMATIC-REACTION BY THE SULFUR FUNCTIONAL-GROUP - A SIMPLE PREPARATION OF OPTICALLY-ACTIVE BETA-HYDROXY NITRILES USING A LIPASE [J].

ITOH, T ;

TAKAGI, Y ;

NISHIYAMA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1521-1524

[7] PREPARATION OF OPTICALLY PURE ALPHA-ALKYL BETA-HYDROXY NITRILES BY THE BAKERS-YEAST REDUCTION [J].

ITOH, TY ;

FUKUDA, T ;

FUJISAWA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (12) :3851-3855

[8] CATALYTIC ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ALKYNYL ALCOHOLS BY ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES AND BY ENANTIOSELECTIVE ALKYLATION OF ALKYNYL ALDEHYDES [J].

NIWA, S ;

SOAI, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :937-943

[9] ENANTIOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CARBONYL-COMPOUNDS - CHIRALITY TRANSFER, MULTIPLICATION, AND AMPLIFICATION [J].

NOYORI, R ;

KITAMURA, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (01) :49-69

[10] ENANTIOSELECTIVE ADDITION OF (Z)-ALKENYLZINC AND (E)-ALKENYLZINC BROMIDES TO ALDEHYDES - ASYMMETRIC-SYNTHESIS OF SEC-ALLYLALCOHOLS [J].

OPPOLZER, W ;

RADINOV, RN .

TETRAHEDRON LETTERS, 1991, 32 (41) :5777-5780

← 1 2 →