Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects

被引：275

作者：

Arnold, LA ^{[1
]}

Imbos, R ^{[1
]}

Mandoli, A ^{[1
]}

de Vries, AHM ^{[1
]}

Naasz, R ^{[1
]}

Feringa, BL ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

TETRAHEDRON | 2000年 / 56卷 / 18期

关键词：

phosphoramidite ligand; copper; enantioselective conjugate addition; enones; non-linear effect; diethyl zinc; catalytic 1,4-addition;

D O I：

10.1016/S0040-4020(00)00142-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of new chiral phosphoramidites was synthesised and tested in the copper-catalysed enantioselective conjugate addition of diethylzinc to cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.'s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic and acyclic enones. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2865 / 2878

页数：14

共 80 条

[11] A new diastereo- and enantioselective copper-catalyzed conversion of alkynyl epoxides into α-allenic alcohols.
Bertozzi, F
Crotti, P
Macchia, F
Pineschi, M
Arnold, A
Feringa, BL
[J]. TETRAHEDRON LETTERS, 1999, 40 (26) : 4893 - 4896
[12] Kinetic implications of nonlinear effects in asymmetric synthesis
Blackmond, DG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (51) : 13349 - 13353
[13] BOERSMA J, 1982, COMPREHENSIVE ORGANO, V2, pCH16
[14] BOLM C, 1992, SYNLETT, P439
[15] OPTICALLY-ACTIVE BIPYRIDINES IN NICKEL CATALYZED ENANTIOSELECTIVE CONJUGATE ADDITION TO ENONES
BOLM, C
EWALD, M
[J]. TETRAHEDRON LETTERS, 1990, 31 (35) : 5011 - 5012
[16] ENANTIOSELECTIVE CONJUGATE ADDITION OF RATIONALLY DESIGNED CHIRAL CUPRATE REAGENTS TO 2-CYCLOALKENONES
COREY, EJ
NAEF, R
HANNON, FJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) : 7114 - 7116
[17] CONJUGATE ADDITION OF DIETHYLZINC TO ENONES CATALYZED BY HOMOGENEOUS AND SUPPORTED CHIRAL NI-COMPLEXES - COOPERATIVE EFFECT OF THE SUPPORT ON ENANTIOSELECTIVITY
CORMA, A
IGLESIAS, M
MARTIN, MV
RUBIO, J
SANCHEZ, F
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (07) : 845 - 848
[18] EXPEDIENT ROUTE TO 3-SUBSTITUTED AND 3,3'-SUBSTITUTED 1,1'-BI-2-NAPHTHOLS BY DIRECTED ORTHO METALATION AND SUZUKI CROSS COUPLING METHODS
COX, PJ
WANG, W
SNIECKUS, V
[J]. TETRAHEDRON LETTERS, 1992, 33 (17) : 2253 - 2256
[19] HOST-GUEST COMPLEXATION .8. MACROCYCLIC POLYETHERS SHAPED BY 2 RIGID SUBSTITUTED DINAPHTHYL OR DITETRALYL UNITS
CRAM, DJ
HELGESON, RC
PEACOCK, SC
KAPLAN, LJ
DOMEIER, LA
MOREAU, P
KOGA, K
MAYER, JM
CHAO, Y
SIEGEL, MG
HOFFMAN, DH
SOGAH, GDY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) : 1930 - 1946
[20] CRAM DJ, 1981, CHEM COMMUN, P625

← 1 2 3 4 5 6 7 8 →