1,4-addition of diethylzinc to cyclohexenone catalyzed by CuOTf-sulfonamide combined system. Evidence supporting a concerted mechanism

被引：18

作者：

Nakano, K ^{[1
]}

Bessho, Y

Kitamura, M

机构：

[1] Nagoya Univ, Res Ctr Mat Sci, Nagoya, Aichi 4648602, Japan

[2] Nagoya Univ, Dept Chem, Nagoya, Aichi 4648602, Japan

来源：

CHEMISTRY LETTERS | 2003年 / 32卷 / 03期

关键词：

D O I：

10.1246/cl.2003.224

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Measurement of C-12/C-13 isotope effect in the Cu(I)/sulfonamide-catalyzed 1,4-addition of diethylzinc to 2-cyclohexenone implies that the reaction proceeds by a concerted mechanism, different to those so far reported for the conventional stoichiometric 1,4-addition of organometallic compounds involving Cu.

引用

页码：224 / 225

页数：2

共 25 条

[1] [Anonymous], COMPREHENSIVE ORGANI
[2] Isotope effects and the mechanism of chlorotrimethylsilane-mediated addition of cuprates to enones
Frantz, DE
Singleton, DA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) : 3288 - 3295
[3] C-13 kinetic isotope effects for the addition of lithium dibutylcuprate to cyclohexenone. Reductive elimination is rate-determining
Frantz, DE
Singleton, DA
Snyder, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) : 3383 - 3384
[4] REACTION OF DIARYL-ZINC COMPOUNDS WITH COPPER(I) SALTS - SYNTHESIS AND CHARACTERIZATION OF ARYLCOPPER(I) COMPOUNDS
HOFSTEE, HK
BOERSMA, J
VANDERKERK, GJM
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 144 (02) : 255 - 261
[5] Quantitative analysis of the chiral amplification in the amino alcohol-promoted asymmetric alkylation of aldehydes with dialkylzincs
Kitamura, M
Suga, S
Oka, H
Noyori, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (38) : 9800 - 9809
[6] Mechanism of asymmetric hydrogenation of α-(acylamino)acrylic esters catalyzed by BINAP-ruthenium(II) diacetate
Kitamura, M
Tsukamoto, M
Bessho, Y
Yoshimura, M
Kobs, U
Widhalm, M
Noyori, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) : 6649 - 6667
[7] Asymmetric addition of dialkylzincs to benzaldehyde derivatives catalyzed by chiral β-amino alcohols.: Evidence for the monomeric alkylzinc aminoalkoxide as catalyst
Kitamura, M
Oka, H
Noyori, R
[J]. TETRAHEDRON, 1999, 55 (12) : 3605 - 3614
[8] Homochiral and heterochiral dimers of the methylzinc alkoxide formed from dimethylzinc and enantiomeric 3-exo-(dimethylamino)isoborneol - Origin of the distinct differences in solution-phase behavior and crystal structures
Kitamura, M
Yamakawa, M
Oka, H
Suga, S
Noyori, R
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (09) : 1173 - 1181
[9] Conjugate addition of diorganozincs to alpha,beta-unsaturated ketones catalyzed by a copper(I)-sulfonamide combined system
Kitamura, M
Miki, T
Nakano, K
Noyori, R
[J]. TETRAHEDRON LETTERS, 1996, 37 (29) : 5141 - 5144
[10] ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES PROMOTED BY CHIRAL AMINO-ALCOHOLS - MECHANISM AND NONLINEAR EFFECT
KITAMURA, M
OKADA, S
SUGA, S
NOYORI, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) : 4028 - 4036

← 1 2 3 →