Chiral 2,2′-bipyridines, 5,6-dihydro-1,10-phenanthrolines and 1,10-phenanthrolines as ligands for enantioselective palladium catalyzed allylic substitution

被引：39
|
作者：
Chelucci, G [1 ]
Saba, A [1 ]
Sanna, G [1 ]
Soccolini, F [1 ]
机构：
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 16期
关键词：
D O I：
10.1016/S0957-4166(00)00296-2
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A number of chiral 5,6-dihydro-1,1-phenanthrolines, 5,6-dihydrobenzo[b]-1,1-phenanthrolines and 5,6,7,8-tetrahydro-2-quinolinylquinoline derived from (-)-pinocarvone were prepared and assessed in the enantioselective palladium catalyzed allylic alkylation 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 drastic reduction of the stereoselectivity of the reaction. Enantioselectivities up to 81% were obtained. (C) 2000 Published by Elsevier Science Ltd.
引用
收藏
页码：3427 / 3438
页数：12
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