Cationic bis(oxazoline) and pyridyl-bis(oxazoline)Cu(II) and Zn(II) Lewis acid catalysts. A comparative study in catalysis of Diels-Alder and aldol reactions

被引:119
作者
Evans, DA
Kozlowski, MC
Tedrow, JS
机构
[1] Dept. of Chem. and Chemical Biology, Harvard University, Cambridge
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
D O I
10.1016/0040-4039(96)01697-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A systematic comparison of the cationic Lewis acidic Cu(II) and Zn(II) catalysts derived from bis(oxazoline), box, and pyridyl-bis(oxazoline), pybox, ligands is presented. Upon screening the catalysts in the Diels-Alder and aldol reactions, the Cu-based catalysts were found to be superior. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:7481 / 7484
页数:4
相关论文
共 12 条
[1]  
[Anonymous], 1987, COMPREHENSIVE COORDI
[2]   DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX [J].
COREY, EJ ;
IMAI, N ;
ZHANG, HY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :728-729
[3]   HIGHLY ENANTIOSELECTIVE CATALYTIC DIELS-ALDER ADDITION PROMOTED BY A CHIRAL BIS(OXAZOLINE)-MAGNESIUM COMPLEX [J].
COREY, EJ ;
ISHIHARA, K .
TETRAHEDRON LETTERS, 1992, 33 (45) :6807-6810
[4]   BIS(IMINE)-COPPER(II) COMPLEXES AS CHIRAL LEWIS-ACID CATALYSTS FOR THE DIELS-ALDER REACTION [J].
EVANS, DA ;
LECTKA, T ;
MILLER, SJ .
TETRAHEDRON LETTERS, 1993, 34 (44) :7027-7030
[5]   C-2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of silylketene acetals to (benzyloxy)acetaldehyde [J].
Evans, DA ;
Murry, JA ;
Kozlowski, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) :5814-5815
[6]   C-2-SYMMETRIC CATIONIC COPPER(II) COMPLEXES AS CHIRAL LEWIS-ACIDS - COUNTERION EFFECTS IN THE ENANTIOSELECTIVE DIELS-ALDER REACTION [J].
EVANS, DA ;
MURRY, JA ;
VONMATT, P ;
NORCROSS, RD ;
MILLER, SJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :798-800
[7]   BIS(OXAZOLINE)COPPER(II) COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE DIELS-ALDER REACTION [J].
EVANS, DA ;
MILLER, SJ ;
LECTKA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6460-6461
[8]   COMPARISON OF THE MOLECULAR-STRUCTURES OF 5-COORDINATE COPPER(II) AND ZINC(II) COMPLEXES OF 2,6-DIACETYLPYRIDINE DIOXIME [J].
NICHOLSON, GA ;
PETERSEN, JL ;
MCCORMICK, BJ .
INORGANIC CHEMISTRY, 1982, 21 (09) :3274-3280
[9]   HIGHLY ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH CHIRAL AND C2-SYMMETRICAL BIS(OXAZOLINYL)PYRIDINE-RHODIUM CATALYSTS [J].
NISHIYAMA, H ;
KONDO, M ;
NAKAMURA, T ;
ITOH, K .
ORGANOMETALLICS, 1991, 10 (02) :500-508
[10]   Lewis acid catalysis of a Diels-Alder reaction in water [J].
Otto, S ;
Bertoncin, F ;
Engberts, JBFN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (33) :7702-7707