A novel example of chiral counteranion induced enantioselective metal catalysis: The importance of ion-pairing in copper-catalyzed olefin aziridination and cyclopropanation

被引:153
作者
Llewellyn, DB [1 ]
Adamson, D [1 ]
Arndtsen, BA [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
D O I
10.1021/ol000303y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A new ion-pairing route to achieve asymmetric catalysis has been observed in the copper-catalyzed aziridination of styrene with a chiral counteranion. Structural studies suggest that enantioinduction occurs via ion-pairing of the cationic copper catalyst in the chiral pocket created by the anion, The degree of asymmetric induction can be tuned with features that affect ion-pairing, such as achiral and chiral ligands, temperature, and solvent polarity.
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页码:4165 / 4168
页数:4
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