Formation of α-dialkylamino alkyllithium intermediates in the reaction of N,N-dialkylamides with PhMe2SiLi followed by a second lithium reagent, and their alkylation, fragmentation, cyclisation and rearrangement by proton transfer

被引：16

作者：

Fleming, I

Mack, SR

Clark, BP

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

[2] Eli Lilly & Co, Lilly Res Ctr Ltd, Windlesham GU20 6PH, Surrey, England

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 06期

关键词：

D O I：

10.1039/a800651b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tertiary amides (RCONMe2) react with PhMe2SiLi, followed by a second lithium reagent NuLi, to give alpha-dialkylamino alkyllithium intermediates R(Me2N)CLiNu that undergo protonation 2 --> 3, alkylation 2a --> 3ab, beta-elimination 5 --> 6, intramolecular attack on an isolated double bond 9 --> 10, intramolecular proton transfer 12, 17 and 22 (arrows), and fragmentation 28 and 34 (arrows), depending upon the structures of the various components R and Nu.

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页码：715 / 716

页数：2

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