Asymmetric addition of achiral organomagnesium reagents or organolithiums to achiral aldehydes or ketones: a review

被引:104
作者
Luderer, Matthew R. [1 ]
Bailey, William F. [2 ]
Luderer, Mark R. [2 ]
Fair, Justin D. [2 ]
Dancer, Robert J. [3 ]
Sommer, Michael Bech [3 ]
机构
[1] Univ Pittsburgh, Dept Nat Sci, Greensburg, PA 15601 USA
[2] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA
[3] H Lundbeck & Co AS, Proc Chem, DK-2500 Copenhagen, Denmark
关键词
3-AMINOPYRROLIDINE LITHIUM AMIDES; HIGHLY ENANTIOSELECTIVE ADDITION; N-BUTYLLITHIUM; GRIGNARD-REAGENTS; CHIRAL LIGANDS; CARBONYL-COMPOUNDS; ALKYLLITHIUM REAGENTS; ALKYLATION REACTIONS; TITANIUM COMPLEXES; TARTARIC ACID;
D O I
10.1016/j.tetasy.2009.03.015
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学];
摘要
The enantioselective preparation of chiral secondary and tertiary alcohols via addition of an achiral organomagnesium reagent or an organolithium to an achiral aldehyde or ketone in a chiral medium is reviewed. The review is written in chronological order and contains 113 references to literature through late 2008. (c) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:981 / 998
页数:18
相关论文
共 116 条
[1]
THE ROLE OF THE PRODUCT IN ASYMMETRIC C-C BOND FORMATION - STOICHIOMETRIC AND CATALYTIC ENANTIOSELECTIVE AUTOINDUCTION [J].
ALBERTS, AH ;
WYNBERG, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (18) :7265-7266
[2]
GRIGNARD SYNTHESIS OF 2-PHENYL-2-BUTANOL IN OPTICALLY ACTIVE SOLVENTS [J].
ALLENTOFF, N ;
WRIGHT, GF .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (01) :1-6
[3]
Enantioselective butylation of aliphatic aldehydes by mixed chiral lithium amide n-BuLi dimers [J].
Arvidsson, PI ;
Davidsson, O ;
Hilmersson, G .
TETRAHEDRON-ASYMMETRY, 1999, 10 (03) :527-534
[4]
Arvidsson PI, 1999, CHEM-EUR J, V5, P2348, DOI 10.1002/(SICI)1521-3765(19990802)5:8<2348::AID-CHEM2348>3.0.CO
[5]
2-A
[6]
Li3[Ln(binol)3]•6THF:: New anhydrous lithium lanthanide binaphtholates and their use in enantioselective alkyl addition to aldehydes [J].
Aspinall, HC ;
Dwyer, JLM ;
Greeves, N ;
Steiner, A .
ORGANOMETALLICS, 1999, 18 (08) :1366-1368
[7]
Synthetic variations based on low-valent chromium:: new developments [J].
Avalos, M ;
Babiano, R ;
Cintas, P ;
Jiménez, JL ;
Palacios, JC .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (03) :169-177
[8]
BATTIONI JP, 1972, B SOC CHIM FR, P2068
[9]
BETTI M, 1940, B SCI FAC CHIM IND B, V1, P2
[10]
BLOMBERG C, 1964, RECL TRAV CHIM PAY B, V83, P1083