CATALYZED ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES

被引：149

作者：

BOLM, C ^{[1
]}

SCHLINGLOFF, G ^{[1
]}

HARMS, K ^{[1
]}

机构：

[1] UNIV MARBURG, FACHBEREICH CHEM, W-3550 MARBURG, GERMANY

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 05期

关键词：

ASYMMETRIC ALKYLATION; PYRIDINES; OPTICALLY ACTIVE; CHIRAL LIGANDS; ASYMMETRIC SYNTHESIS; ENANTIOSELECTIVE CATALYSIS;

D O I：

10.1002/cber.19921250529

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective alkylation of a variety of aldehydes with diethylzinc was achieved by using catalytic amounts of optically active pyridines and C2-symmetric 2-2'-bipyridines. The products were obtained in good yields with high enantioselectivities. Steric factors of the catalyst structure which govern the stereoselectivity were revealed, and important reaction intermediates were identified by spectroscopic means and single-crystal X-ray diffraction. The effect of additives on the optical purity of the product was studied. A strong asymmetric amplification was found with catalysts of low ee's.

引用

页码：1191 / 1203

页数：13

共 123 条

[71] ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ARYLALDEHYDES CATALYZED BY CHIRAL COBALT(II) AND PALLADIUM(II) COMPLEXES
OGUNI, N
OMI, T
YAMAMOTO, Y
NAKAMURA, A
[J]. CHEMISTRY LETTERS, 1983, (06) : 841 - 842
[72] ENANTIOSELECTIVE SYNTHESIS OF SEC-ALLYLALCOHOLS BY CATALYTIC ASYMMETRIC ADDITION OF DIVINYLZINC TO ALDEHYDES
OPPOLZER, W
RADINOV, RN
[J]. TETRAHEDRON LETTERS, 1988, 29 (44) : 5645 - 5648
[73] OPPOLZER W, 1991, COMMUNICATION 1016
[74] CATALYTIC HOMO-REFORMATSKY REACTION - AMBIDENT CHEMICAL REACTIVITIES OF THE ZINC HOMOENOLATE OF PROPIONATE
OSHINO, H
NAKAMURA, E
KUWAJIMA, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15) : 2802 - 2804
[75] 3-DIMENSIONAL MACROCYCLIC ENCAPSULATION REACTIONS .2. SYNTHESIS AND PROPERTIES OF NONOCTAHEDRAL CLATHRO CHELATES DERIVED FROM TRIS(2-ALDOXIMO-6-PYRIDYL)PHOSPHINE AND BORON TRIFLUORIDE OR TETRAFLUOROBORATE
PARKS, JE
WAGNER, BE
HOLM, RH
[J]. INORGANIC CHEMISTRY, 1971, 10 (11) : 2472 - &
[76] PARSHALL GW, 1988, CHEMTECH, V18, P314
[77] TRENDS AND OPPORTUNITIES FOR ORGANOMETALLIC CHEMISTRY IN INDUSTRY
PARSHALL, GW
[J]. ORGANOMETALLICS, 1987, 6 (04) : 687 - 692
[78] PARSHALL GW, 1988, CHEMTECH, V18, P376
[79] PARSHALL GW, 1988, CHEMTECH, V18, P184
[80] Investigations on the dependence of rotatory power on chemical constitution. Part VI. The optical rotatory power of methy-tert-butyl-, methylbenzyl-, methylphenylethyl- and methyl-alpha-naphthyl-carbinols.
Pickard, RH
Kenyon, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1914, 105 : 1115 - 1131

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