Metal-catalyzed silacyclopropanation of mono- and disubstituted alkenes.
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.
Ciraković
Jelena
J
Department of Chemistry, University of California, Irvine 92697-2025, USA.
Driver
Tom G
TG
Woerpel
K A
KA
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*
D000475:Alkenes; D006571:Heterocyclic Compounds; D008670:Metals; D017646:Organosilicon Compounds