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

页码：2094 / 2097

页数：4

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