ENANTIOSELECTIVE 1,4-ADDITIONS OF ORGANOMETALLIC COMPOUNDS TO CONJUGATED SYSTEMS IN THE CHIRAL MEDIUM DDB

被引：100

作者：

LANGER, W

SEEBACH, D

机构：

[1] UNIV ZURICH,ETH ZENTRUM,ORGAN CHEM LAB,CH-8092 ZURICH,SWITZERLAND

[2] UNIV GIESSEN,INST ORGAN CHEM,D-6300 GIESSEN,FED REP GER

来源：

HELVETICA CHIMICA ACTA | 1979年 / 62卷 / 06期

关键词：

D O I：

10.1002/hlca.19790620604

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective 1,4‐additions of organometallic compounds to conjugated systems in the chiral medium DDB The chiral methoxyamine DDB is used as a cosolvent to add achiral Li‐, Cu‐, and Zn‐organic compounds enantioselectively to prochiral β‐carbon atoms of α, β‐unsaturated aldehydes, ketones, nitro compounds and ketene‐thioacetals (Tables 1 and 2). The selectivity generally ranges from 55:45 to 63:27, in one case (9b) an enantiomeric excess of 43% was obtained. Copyright © 1979 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：1710 / 1722

页数：13

共 63 条

[1] AMINE BISULFITES .2. THEIR USE AS RESOLVING AGENTS FOR ALDEHYDES AND KETONES
ADAMS, R
GARBER, JD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (02) : 522 - 526
[2] [Anonymous], 1969, ANGEW CHEM, V81, P1047
[3] [Anonymous], 1971, ANGEW CHEM, V83, P542
[4] REACTIONS OF NITROARENES WITH GRIGNARD-REAGENTS - GENERAL METHOD OF SYNTHESIS OF ALKYL-NITROSO-SUBSTITUTED BICYCLIC AROMATIC SYSTEMS
BARTOLI, G
LEARDINI, R
MEDICI, A
ROSINI, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (07): : 692 - 696
[5] BOWLUS SB, 1975, TETRAHEDRON LETT, P3591
[6] OXYGEN-INDUCED REACTIONS OF ORGANOBORANES WITH INERT ALPHA,BETA-UNSATURATED CARBONYL DERIVATIVES . A CONVENIENT NEW ALDEHYDE AND KETONE SYNTHESIS VIA HYDROBORATION
BROWN, HC
KABALKA, GW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) : 714 - &
[7] REACTIVE ORGANOMAGNESIUM REDUCING AGENTS .5. ASYMMETRIC INDUCTION IN REDUCTION OF ALPHA-BETA ETHYLENIC CHIRAL ESTERS
CABARET, D
WELVART, Z
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 80 (02) : 185 - 198
[8] COHEN T, 1978, TETRAHEDRON LETT, P3533
[9] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
DULL, DL
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
[10] REACTIONS OF POLYMETALLATED CARBONYL-COMPOUNDS WITH NITROOLEFINES A NEW RING-CLOSURE AND ANELLATION METHOD
EHRIG, V
SEEBACH, D
[J]. CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (06): : 1961 - 1973

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