Enantioselective copper(I) catalyzed 1,4-addition of diethylzinc to cyclohexenone: Asymmetric induction as an unexpected source of structural information

被引：46

作者：

Wendisch, V ^{[1
]}

Sewald, N ^{[1
]}

机构：

[1] UNIV LEIPZIG,DEPT ORGAN CHEM,D-04103 LEIPZIG,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 08期

关键词：

catalytic asymmetric synthesis; conjugate addition; diethylzinc; copper(I) salts; sulfonamides;

D O I：

10.1016/S0957-4166(97)00102-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The conjugate addition of diethylzinc to cyclohexenone in the presence of catalytic amounts of homochiral sulfonamides and different copper(I) salts has been examined. The anion of the copper(I) salt significantly influences the topicity of the 1,4-addition. With the same absolute configuration of the chiral catalyst, CuCN favours formation of R-3-ethylcyclohexanone, while the S-configured product predominates for all other copper(I) salts used. This clearly hints towards structural differences between the catalytically active complexes. (C) 1997 Elsevier Science Ltd.

引用

页码：1253 / 1257

页数：5

共 51 条

[1] AN EASY AND FAST WAY TO DETERMINE THE ENANTIOMERIC PURITY OF SUBSTITUTED CYCLANONES
ALEXAKIS, A
FRUTOS, JC
MANGENEY, P
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2431 - 2434
[2] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS
ALEXAKIS, A
FRUTOS, J
MANGENEY, P
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2427 - 2430
[3] STEREOCHEMICAL EFFECTS OF TRIMETHYLSILYL CHLORIDE (TMSCL) ON THE CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS
ALEXAKIS, A
SEDRANI, R
MANGENEY, P
[J]. TETRAHEDRON LETTERS, 1990, 31 (03) : 345 - 348
[4] ALEXAKIS A, ORGANIC SYNTHESIS VI
[5] ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO CHALCONES USING NICL2-CHIRAL BETA-DIAMINE COMPLEX AS CATALYST
ASAMI, M
USUI, K
HIGUCHI, S
INOUE, S
[J]. CHEMISTRY LETTERS, 1994, (02) : 297 - 298
[6] Bertz S.H., 1996, J CHEM SOC CHEM COMM, P815
[7] NEW COPPER CHEMISTRY .20. LITHIUM CYANOCUPRATES, RCU(CN)LI - 1ST OBSERVATION OF 2-BOND C-13-C-13 NMR COUPLINGS IN ORGANOCUPRATES
BERTZ, SH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) : 5470 - 5471
[8] NEW COPPER CHEMISTRY .17. HIGHER-ORDER CYANOCUPRATES - ARE THEY REAL
BERTZ, SH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) : 4031 - 4032
[9] PHENYLCOPPER(I) AND DIPHENYLCUPRATE(I) - CHARACTERIZATION OF AGGREGATION STATES BY 13C NMR-SPECTROSCOPY
BERTZ, SH
DABBAGH, G
HE, XM
POWER, PP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) : 11640 - 11641
[10] CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF DIALKYLZINC COMPOUNDS TO CHALCONES
BOLM, C
EWALD, M
FELDER, M
[J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05): : 1205 - 1215

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