Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects

被引:275
作者
Arnold, LA [1 ]
Imbos, R [1 ]
Mandoli, A [1 ]
de Vries, AHM [1 ]
Naasz, R [1 ]
Feringa, BL [1 ]
机构
[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
关键词
phosphoramidite ligand; copper; enantioselective conjugate addition; enones; non-linear effect; diethyl zinc; catalytic 1,4-addition;
D O I
10.1016/S0040-4020(00)00142-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of new chiral phosphoramidites was synthesised and tested in the copper-catalysed enantioselective conjugate addition of diethylzinc to cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.'s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic and acyclic enones. (C) 2000 Elsevier Science Ltd. All rights reserved.
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页码:2865 / 2878
页数:14
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