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The Reactivity of Epoxides with Lithium 2,2,6,6-Tetramethylpiperidide in Combination with Organolithiums or Grignard Reagents

David M. Hodgson,* Matthew J. Fleming and Steven J. Stanway

*Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom, Email:

D. M. Hodgson, M. J. Fleming, S. J. Stanway, J. Org. Chem., 2007, 72, 4763-4773.

DOI: 10.1021/jo070291v

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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.

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possible origin of alkene stereochemistry

Key Words

Styrenes, Dienes

ID: J42-Y2007-2000