Journal
TETRAHEDRON
Volume 57, Issue 24, Pages 5045-5054Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00348-9
Keywords
Peterson-type olefination reaction; vinylsilanes; silyl alcohols
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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.
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