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2005
Alkenes
P 0023
05- 059
Alkenes from Terminal Epoxides Using Lithium 2,2,6,6-Tetramethylpiperidide
and Organolithiums or Grignard Reagents. — The title method broadens significantly the use of epoxides as regio- and stereo-defined vinyl cation equivalents. The
ability of a lithium amide (LiTMP) and a organolithium compound (or Grignard reagents), present in the same flask, to operate apparently independently of each other
but in a defined sequence on a terminal epoxide results in formation of alkenes in a
highly (E)-selective manner. Performance of the same reactions in the absence of
LiTMP affords the corresponding homoallylic secondary alcohols from direct
ring-opening of the epoxide (to be continued). — (HODGSON*, D. M.; FLEMING,
M. J.; STANWAY, S. J.; J. Am. Chem. Soc. 126 (2004) 39, 12250-pp; Chem. Res.
Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3TA, UK; Eng.) — Klein
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