Catalytic Synthesis of Enantiopure Chiral Alcohols via Addition of Grignard Reagents to Carbonyl Compounds

被引:86
作者
Collados, Juan F. [1 ]
Sola, Ricard [2 ]
Harutyunyan, Syuzanna R. [1 ]
Macia, Beatriz [2 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands
[2] Manchester Metropolitan Univ, Fac Sci & Engn, Div Chem & Environm Sci, John Dalton Bldg,Oxford Rd, Manchester M1 SGD, Lancs, England
基金
英国工程与自然科学研究理事会;
关键词
Grignard reagents; carbonyl compound; 1,2-addition reaction; enantioselective catalysis; titanium; copper; HIGHLY ENANTIOSELECTIVE ADDITION; CROSS-COUPLING REACTIONS; ASYMMETRIC ADDITION; ORGANOMAGNESIUM REAGENTS; DIORGANOZINC REAGENTS; TITANIUM COMPLEXES; TRIALKYLALUMINUM ADDITION; ORGANOMETALLIC REAGENTS; ORGANOZINC REAGENTS; EXCHANGE-REACTION;
D O I
10.1021/acscatal.5b02832
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Remarkable progress in the enantioselective addition of Grignard reagents to carbonyl compounds has been made over the past decade. This enantioselective transformation now allows the use of these challenging reactive nucleophiles for the formation of chiral alcohols using catalytic amounts of chiral ligands. This review summarizes the developments in this area.
引用
收藏
页码:1952 / 1970
页数:19
相关论文
共 108 条
[1]   CONCERNING THE EFFECTS OF ADDED SALTS ON THE STEREOSELECTIVITY AND RATE OF ORGANOMETALLIC COMPOUND ADDITION TO KETONES [J].
ASHBY, EC ;
NODING, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) :4371-4377
[2]   Insight into the mechanism of the asymmetric addition of alkyl groups to aldehydes catalyzed by titanium - BINOLate species [J].
Balsells, J ;
Davis, TJ ;
Carroll, P ;
Walsh, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) :10336-10348
[3]   The X-ray Crystal Structure of a Cuprate-Carbonyl π-Complex [J].
Bertz, Steven H. ;
Hardin, Richard A. ;
Heavey, Thomas J. ;
Ogle, Craig A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (39) :10250-10252
[4]   Asymmetric Addition of Diorganozinc Reagents to Aldehydes and Ketones [J].
Binder, Caitlin M. ;
Singaram, Bakthan .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2011, 43 (02) :139-208
[5]   Remarkably stable (Me3Al)2•DABCO and stereoselective nickel-catalyzed AlR3 (R = Me, Et) additions to aldehydes [J].
Biswas, K ;
Prieto, O ;
Goldsmith, PJ ;
Woodward, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (15) :2232-2234
[6]  
Biswas K., 2005, ANGEW CHEM, V117, P2272
[7]  
Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
[8]  
Bolm C., 2001, ANGEW CHEM, V113, P3382
[9]  
Boymond L, 1998, ANGEW CHEM INT EDIT, V37, P1701, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1701::AID-ANIE1701>3.0.CO
[10]  
2-U