Steric versus electronic effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines

被引:36
作者
Chelucci, G
Deriu, S
Pinna, GA
Saba, A
Valenti, R
机构
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
[2] Univ Sassari, Dipartimento Farmaco Chim Tossicol, I-07100 Sassari, Italy
关键词
D O I
10.1016/S0957-4166(99)00368-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral oxazolinylpyridines bearing an oxazolinyl [bis(oxazolinyl)pyridines] or a cyano group in the 6-position of the pyridine ring were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. The electronic and steric properties of substituents hardly affected either the catalytic activity or the enantioselectivity of the substitution reaction. Enantioselectivities up to 94% were obtained. (C) 1999 Elsevier Science Ltd. All rights reserved.
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收藏
页码:3803 / 3809
页数:7
相关论文
共 20 条
[1]  
BANCKS R, 1974, CHEM IND-LONDON, V15, P617
[2]   First-principles investigation of enantioselective catalysis: Asymmetric allylic amination with Pd complexes bearing P,N-ligands [J].
Blochl, PE ;
Togni, A .
ORGANOMETALLICS, 1996, 15 (20) :4125-4132
[3]   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
[4]   Palladium-catalyzed allylic alkylation using pyridino-oxazolines and quinolino-oxazolines as ligands - influence of steric factors [J].
Bremberg, U ;
Rahm, F ;
Moberg, C .
TETRAHEDRON-ASYMMETRY, 1998, 9 (19) :3437-3443
[5]   Steric effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation using chiral oxazolinylpyridines [J].
Chelucci, G ;
Medici, S ;
Saba, A .
TETRAHEDRON-ASYMMETRY, 1999, 10 (03) :543-550
[6]   New chiral C-2-symmetric bis(oxazolinylpyridinyl)dioxolane ligands for asymmetric catalysis: palladium catalysed allylic substitution [J].
Chelucci, G .
TETRAHEDRON-ASYMMETRY, 1997, 8 (16) :2667-2670
[7]   Remote electronic control of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines [J].
Chelucci, G ;
Deriu, SP ;
Saba, A ;
Valenti, R .
TETRAHEDRON-ASYMMETRY, 1999, 10 (08) :1457-1464
[8]   Chiral pyridylmethyl- and quinolinyl-oxazolines as ligands for enantioselective palladium-catalyzed allylic alkylation [J].
Chelucci, G ;
Gladiali, S ;
Saba, A .
TETRAHEDRON-ASYMMETRY, 1999, 10 (07) :1393-1400
[9]   SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION [J].
FROST, CG ;
HOWARTH, J ;
WILLIAMS, JMJ .
TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1089-1122
[10]  
GLUBOKOVSKIKH LK, 1985, IZV AKAD NAUK KAZ K, V3, P90