ENANTIOSELECTIVE PALLADIUM CATALYZED ALLYLIC SUBSTITUTION WITH THIENYL OXAZOLINE LIGANDS

被引:117
作者
FROST, CG [1 ]
WILLIAMS, JMJ [1 ]
机构
[1] LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)91990-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Homochiral thienyl oxazolines have been employed as ligands for enantioselective palladium catalysed allylic substitution. The ligands are straightforward to prepare in one step from commercially available materials and afford good levels of asymmetric induction in the catalytic allylic substitution process of up to 81% ee. The stereochemical outcome is described in terms of steric and electronic factors.
引用
收藏
页码:2015 / 2018
页数:4
相关论文
共 24 条
[1]  
BALAVOINE JC, 1989, TETRAHEDRON LETT, V30, P514
[2]   SYNTHESIS OF OPTICALLY-ACTIVE BIS(2-OXAZOLINES) - CRYSTAL-STRUCTURE OF A 1,2-BIS(2-OXAZOLINYL)BENZENE.ZNCL2 COMPLEX [J].
BOLM, C ;
WEICKHARDT, K ;
ZEHNDER, M ;
RANFF, T .
CHEMISCHE BERICHTE, 1991, 124 (05) :1173-1180
[3]   ASYMMETRIC CATALYSIS .44. ENANTIOSELECTIVE MONOPHENYLATION OF DIOLS WITH CU(OAC)2/PYRIDINYLOXAZOLINE CATALYSTS [J].
BRUNNER, H ;
OBERMANN, U ;
WIMMER, P .
ORGANOMETALLICS, 1989, 8 (03) :821-826
[4]   ENANTIOSELECTIVE HOMOGENEOUS CATALYSIS INVOLVING TRANSITION-METAL ALLYL INTERMEDIATES [J].
CONSIGLIO, G ;
WAYMOUTH, RM .
CHEMICAL REVIEWS, 1989, 89 (01) :257-276
[5]   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
[6]   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
[7]  
DAWSON GR, UNPUB
[8]   BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].
EVANS, DA ;
WOERPEL, KA ;
HINMAN, MM ;
FAUL, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728
[9]   SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION [J].
FROST, CG ;
HOWARTH, J ;
WILLIAMS, JMJ .
TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1089-1122
[10]   LIBH4(NABH4) ME3SICL, AN UNUSUALLY STRONG AND VERSATILE REDUCING AGENT [J].
GIANNIS, A ;
SANDHOFF, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (02) :218-220