Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents

被引:64
作者
Endo, Kohei [1 ]
Ogawa, Mika [1 ]
Shibata, Takanori [1 ]
机构
[1] Waseda Univ, Dept Chem & Biochem, Sch Adv Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan
关键词
alkylation; synthetic methods; copper; Michael addition; zinc; MANNICH-TYPE REACTION; BETA-AMINO ALCOHOLS; GRIGNARD-REAGENTS; ET2ZN/LINKED-BINOL COMPLEX; ACYCLIC ENONES; ENANTIOSELECTIVE HYDROGENATION; QUATERNARY CENTERS; MICHAEL REACTION; ALDOL REACTION; LINKED-BINOL;
D O I
10.1002/anie.200906839
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) A whole lot o' metal: An efficient copper-catalyzed asymmetric conjugate addition was achieved using a binol-derived ligand. The catalytic system has a turnover number of 2000, and the excellent cata-lytic performance could be attributed to the generation of a multinuclear complex such as 1. binol = 2, 2'-dihydroxy-l, 1'-binaphthyl. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2410 / 2413
页数:4
相关论文
共 40 条
[1]   Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].
Alexakis, A. ;
Backvall, J. E. ;
Krause, N. ;
Pamies, O. ;
Dieguez, M. .
CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823
[2]  
[Anonymous], ANGEW CHEM
[3]  
[Anonymous], ANGEW CHEM
[4]  
Bernardinelli, 2007, ANGEW CHEM, V119, P7606
[5]   A bench-stable homodinuclear Ni2-chiff base complex for catalytic asymmetric synthesis of α-tetrasubstituted anti-α,β-diamino acid surrogates [J].
Chen, Zhihua ;
Morimoto, Hiroyuki ;
Matsunaga, Shigeki ;
Shibasaki, Masakatsu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (07) :2170-+
[6]   Enantioselective copper-catalyzed conjugate addition to trisubstituted cyclohexenones: Construction of stereogenic quaternary centers [J].
d'Augustin, M ;
Palais, L ;
Alexakis, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) :1376-1378
[7]  
d'Augustin M, 2005, ANGEW CHEM, V117, P1400, DOI DOI 10.1002/ANGE.200462137
[8]  
den Hartog T., 2008, Angew. Chem. Int. Ed, V120, P404
[9]   Catalytic enantioselective 1,6-conjugate addition of Grignard reagents to linear dienoates [J].
den Hartog, Tim ;
Harutyunyan, Syuzanna R. ;
Font, Daniel ;
Minnaard, Adriaan J. ;
Feringa, Ben L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (02) :398-401
[10]   syn-selective catalytic asymmetric nitro-Mannich reactions using a heterobimetallic Cu-Sm-Schiff base complex [J].
Handa, Shinya ;
Gnanadesikan, Vijay ;
Matsunaga, Shigeki ;
Shibasaki, Masakatsu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) :4900-+