期刊
ORGANIC LETTERS
卷 13, 期 8, 页码 2094-2097出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol200509c
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资金
- NRW Graduate School of Chemistry
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.
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