Tert-butyldiphenylsilylmethyl triflate: Preparation and dipolar cycloaddition reactions of 1-(tert-butyldiphenylsilymethyl)-6-cyano-4-methyl-1,2,5,6-tetrahydropyridi ne

摘要

Alkylation of substituted pyridines with tert-butyldiphenylsilylmethyl triflate provides N-[tert-butyldiphenylsilylmethyl]pyridinium triflates in excellent yields. Reductive cyanation of the pyridinium triflates provides 1-(tert-butyldiphenylsilylmethyl)-6-cyano-1,2,5,6-tetrahydropyridines, azomethine ylid precursors, in modest yields. An unexpected dipolar cycloaddition reaction of an ylid derived from the title 6-cyanopiperidine is described. [References: 17]