2002/07/19 by Jelena Ćiraković, Tom G. Driver, K. A. Woerpel · 2 citations
Chemistry · #Cyclopropane Reaction Mechanisms #Organoboron and organosilicon chemistry #Synthetic Organic Chemistry Methods
paper · doi:10.1021/ja020566i
openalex publication_date 2002/07/19 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01
As an alternative to the strongly reducing conditions necessary for the formation of silacyclopropanes, silylene transfer was developed as a mild, functional group tolerant method of silacyclopropanation. Complex silacyclopropanes were formed from functionalized alkenes using cyclohexane di-tert-butyl silacyclopropane, 1, as the source of t-Bu(2)Si. Di-tert-butyl silylene can be generated from 1 through the use of a catalytic amount of a metal salt. At -27 degrees C, silver triflate catalyzes the transfer of t-Bu(2)Si from 1 to mono- and disubstituted alkenes stereospecifically and diastereoselectively. In situ functionalization of silacyclopropanes with catalytic zinc bromide and methyl formate provides for an expedient one-flask synthesis of complex oxasilacyclopentanes from alkenes.