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:
david.hodgson
chem.ox.ac.uk
D. M. Hodgson, M. J. Fleming, S. J. Stanway, J. Org. Chem., 2007, 72, 4763-4773.
DOI: 10.1021/jo070291v
see article for more reactions
Abstract
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.
see article for more reactions
see article for more examples
possible origin of alkene stereochemistry
Key Words
ID: J42-Y2007-2000
