Unexpected reversal of the enantioselectivity using chiral quinolylmethyl- and acridininyloxazolines as ligands for asymmetric palladium-catalyzed allylic alkylation

被引：22
作者：
Chelucci, G
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
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 19期
关键词：
D O I：
10.1016/S0957-4166(00)00358-X
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
New chiral quinolylmethyloxazolines and acridininyloxazolines were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate. The introduction of a benzo-fused substituent on the pyridine ring not containing the chiral backbone resulted in the switch of the expected chiral sense of enantioselection of the reaction. Enantiomeric excesses up to 78% were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.
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页码：4027 / 4036
页数：10
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