The reactivity of epoxides with lithium 2, 2, 6, 6-tetramethylpiperidide in combination with organolithiums or Grignard reagents

DM Hodgson, MJ Fleming…

Index: Hodgson, David M.; Fleming, Matthew J.; Stanway, Steven J. Journal of Organic Chemistry, 2007 , vol. 72, # 13 p. 4763 - 4773

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Citation Number: 28

Abstract

The scope and limitations of lithium 2, 2, 6, 6-tetramethylpiperidide (LTMP)-modified reductive alkylation of epoxides is detailed. A variety of organolithiums are added to terminal and 2, 2-disubstituted epoxides in the presence of LTMP to generate alkenes in a completely regio-and highly stereoselective manner. Arylated alkenes, dienes, allylsilanes, and enynes are accessed using this procedure. The methodology is applied in the ...