SUBTLE EFFECTS IN THE ASYMMETRIC EPOXIDATION - DEPENDENCE OF KINETIC RESOLUTION EFFICIENCY ON THE MONODENTATE ALKOXIDE LIGANDS OF THE BYSTANDER TITANIUM CENTER

被引:34
作者
MCKEE, BH [1 ]
KALANTAR, TH [1 ]
SHARPLESS, KB [1 ]
机构
[1] MIT, DEPT CHEM, CAMBRIDGE, MA 02139 USA
关键词
D O I
10.1021/jo00025a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Complexes of diisopropyl tartrate and Ti (O(t)Bu)4 were found to catalyze the kinetic resolution of racemic, secondary allylic alcohols with surprisingly low efficiency relative to those generated from Ti(O(i)Pr)4. This effect is documented and its implications are discussed.
引用
收藏
页码:6966 / 6968
页数:3
相关论文
共 8 条
[1]   TARTRATE-LIKE LIGANDS IN THE ASYMMETRIC EPOXIDATION [J].
BURNS, CJ ;
MARTIN, CA ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2826-2834
[2]   STUDIES ON THE MECHANISM OF THE ASYMMETRIC EPOXIDATION - A LIGAND VARIATION APPROACH [J].
CARLIER, PR ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4016-4018
[3]  
FINN MG, 1985, ASYMMETRIC SYNTHESIS, V5, pCH8
[4]  
KALANTAR TH, 1990, THESIS MIT
[5]  
KO SY, 1986, J ORG CHEM, V51, P5143
[6]   KINETIC RESOLUTION OF RACEMIC ALLYLIC ALCOHOLS BY ENANTIOSELECTIVE EPOXIDATION - A ROUTE TO SUBSTANCES OF ABSOLUTE ENANTIOMERIC PURITY [J].
MARTIN, VS ;
WOODARD, SS ;
KATSUKI, T ;
YAMADA, Y ;
IKEDA, M ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6237-6240
[7]   ON THE MECHANISM OF TITANIUM-TARTRATE CATALYZED ASYMMETRIC EPOXIDATION [J].
SHARPLESS, KB ;
WOODARD, SS ;
FINN, MG .
PURE AND APPLIED CHEMISTRY, 1983, 55 (11) :1823-1836
[8]   MECHANISM OF ASYMMETRIC EPOXIDATION .1. KINETICS [J].
WOODARD, SS ;
FINN, MG ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :106-113