Synthesis of gamma-methylene oxacycles and alpha- and beta-alkylidene lactones via silicon-assisted ring opening of cyclopropyl carbinols.
Cyclopropyl carbinols bearing a (tert-butyldiphenylsilyl)methyl substituent undergo silicon-assisted regioselective ring cleavage and the resulting beta-silyl carbocation is intramolecularly trapped with hydroxy and ester functions to generate gamma-methylene oxacycles and alpha- and beta-alkylidene lactones without the cleavage of the silicon function.
Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India. vijendra@iitk.ac.in
Veejendra K
VK
Yadav
Rengarajan
R
Balamurugan