Activation of the Si-B Linkage: Copper-Catalyzed Addition of Nucleophilic Silicon to Imines

被引：79
|
作者：
Vyas, Devendra J. [1 ]
Froehlich, Roland [1 ]
Oestreich, Martin [1 ]
机构：
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 08期
关键词：
CONJUGATE SILYL TRANSFER; ASYMMETRIC-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; INHIBITORS; ESTERS; 1,4-ADDITION; ALDEHYDES;
D O I：
10.1021/ol200509c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Activation of the Si-B bond through copper-catalyzed transmetalation quickly developed into a practical method to generate Cu-Si reagents. These silicon nucleophiles cleanly add to aldehyde-derived imine electrophiles to form alpha-silylated amines in protic media, and no carbon-to-nitrogen Brook-type rearrangement of the intermediate anion is observed. Aside from electron-withdrawing groups at the imine nitrogen atom, for example, SO(2)Tol and P(O)Ph-2, previously delicate nitrogen substituents such as phenyl or benzhydryl are tolerated. The same protocol also allows the unprecedented addition to representative ketone-derived imines.
引用
收藏
页码：2094 / 2097
页数：4
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