Facile generation of [bis(2-pyridyldimethylsilyl)methyl]lithium and its reaction with carbonyl compounds. New method for the stereoselective synthesis of vinylsilanes

The generation of (2-PyMe2Si)(2)CHLi was easily accomplished by the deprotonation of (2-PyMe2Si)(2)CH2 using n-BuLi in Et2O. The H-1 NMR analysis of (2-PyMe2Si)(2)CHLi in Et2O-d(10) revealed the coordination of both pyridyl groups to lithium. Thus generated (2-PyMe2Si)2CHLi was found to react with a variety of aldehydes and ketones to give the corresponding vinylsilanes in extremely high yields with complete stereoselectivities (>99% E). (C) 2001 Elsevier Science Ltd. All rights reserved.