Catalytic asymmetric ring opening of epoxides to chlorohydrins with mild chloride donors and enantiopure titanium complexes

被引:25
作者
Bruns, S [1 ]
Haufe, G [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Berlin, Germany
关键词
D O I
10.1016/S0957-4166(99)00141-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The ring opening of symmetric and racemic epoxides with dilithium tetrachlorocuprate or trimethylsilyl chloride in the presence of titanium (R,R)-(+)-TADDOLates or a titanium (R)-(+)-BINOL complex gave vicinal chlorohydrins or their TMS ethers with maximum 36% enantiomeric excess. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1563 / 1569
页数:7
相关论文
共 38 条
[1]  
ANIIS AD, 1998, ANGEW CHEM, V110, P2010
[2]  
Annis DA, 1998, ANGEW CHEM INT EDIT, V37, P1907, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1907::AID-ANIE1907>3.0.CO
[3]  
2-A
[4]  
BECK AK, 1991, CHIMIA, V45, P238
[5]   STEREOCHEMISTRY OF ADDITIONS OF ACIDS TO STILBENE AND STYRENE OXIDES [J].
BERTI, G ;
BOTTARI, F ;
FERRARIN.PL ;
MACCHIA, B .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (12) :4091-&
[6]   REGIOSELECTIVE AND CHEMOSELECTIVE SYNTHESIS OF HALOHYDRINS BY CLEAVAGE OF OXIRANES WITH METAL-HALIDES [J].
BONINI, C ;
RIGHI, G .
SYNTHESIS-STUTTGART, 1994, (03) :225-238
[7]   DILITHIUM TETRACHLOROCUPRATE - A REAGENT FOR REGIOSELECTIVE CLEAVAGE OF EPOXIDES TO CHLOROHYDRINS [J].
CIACCIO, JA ;
ADDESS, KJ ;
BELL, TW .
TETRAHEDRON LETTERS, 1986, 27 (32) :3697-3700
[8]   Discovery of chiral catalysts through ligand diversity: Ti-catalyzed enantioselective addition of TMSCN to meso epoxides [J].
Cole, BM ;
Shimizu, KD ;
Krueger, CA ;
Harrity, JPA ;
Snapper, ML ;
Hoveyda, AH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1668-1671
[9]  
COLE BM, 1996, ANGEW CHEM, V108, P1776
[10]  
COLEMAN GH, 1941, ORG SYNTH, V1, P158