Titanium(IV) alkoxide ligand exchange with α-hydroxy acids:: The enantioselective aldol addition

被引:33
作者
Mahrwald, R [1 ]
机构
[1] Humboldt Univ, Inst Organ & Bioorgan Chem, D-10115 Berlin, Germany
关键词
D O I
10.1021/ol0002727
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ligand exchange of titanium(IV) alkoxides with alpha -hydroxy acids presents an unexpected and novel approach to enantioselective aldol additions of aldehydes and ketones. The aldol products were isolated in a high degree of syn-diastereoselectivity. High enantioselectivities were observed by using simple optically pure alpha -hydroxy acids in this novel aldol addition.
引用
收藏
页码:4011 / 4012
页数:2
相关论文
共 20 条
[1]   MECHANISTIC STUDIES IN STRONG ACIDS .10. ACID-CATALYZED ENOLIZATION AND ALDOL CONDENSATION OF ACETALDEHYDE [J].
BAIGRIE, LM ;
COX, RA ;
SLEBOCKATILK, H ;
TENCER, M ;
TIDWELL, TT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) :3640-3645
[2]   RECENT ADVANCES IN STEREOSELECTIVE ALDOL REACTIONS OF ESTER AND THIOESTER ENOLATES [J].
BRAUN, M ;
SACHA, H .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1993, 335 (08) :653-668
[3]  
BRAUN M, 1995, HOUBEN WEYL, P1603
[4]  
DEALS C, 1998, SYNTHETIC COMMUN, V28, P2613
[5]  
ENDERS D, 1988, ANGEW CHEM, V100, P594
[6]  
Evans D. A., 1982, TOP STEREOCHEM, V13, P1, DOI DOI 10.1002/9780470147221.CHL
[7]   CHIRAL ENOLATE DESIGN [J].
EVANS, DA ;
TAKACS, JM ;
MCGEE, LR ;
ENNIS, MD ;
MATHRE, DJ ;
BARTROLI, J .
PURE AND APPLIED CHEMISTRY, 1981, 53 (06) :1109-1127
[8]  
Heathcock C. H., 1990, ALDRICHIM ACTA, V23, P99
[9]  
Heathcock C. H., 1992, MODERN SYNTHETIC MET, P1
[10]  
Heathcock C. H., 1991, COMPREHENSIVE ORGANI, V2, P133, DOI [10.1016/B978-0-08-052349-1.00027-5, DOI 10.1016/B978-0-08-052349-1.00027-5]