The Journal of Organic Chemistry

Alkylation of 2-lithio-N-methylpiperidines and-pyrrolidines: scope, limitations, and stereochemistry

RE Gawley, Q Zhang

文献索引：Gawley, Robert E.; Zhang, Qianhui Journal of Organic Chemistry, 1995 , vol. 60, # 18 p. 5763 - 5769

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被引用次数: 90

摘要

The scope and limitations of the alkylation of racemic and nonracemic 2-lithiopiperidines and-pyrrolidines, obtained by transmetalation of the corresponding stannanes, is reported. These organolithiums react with a variety of electrophiles to afford 2-substituted pyrrolidines and piperidines in excellent yield. With primary alkyl halides the reaction proceeds with net inversion of configuration at the metal-bearing carbon in the piperidines; in the ...