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Synlett 1997; 1997(9): 1045-1046
DOI: 10.1055/s-1997-1551
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Wittig Rearrangement of α-(Propargyloxy)alkyllithiums: Periselectivity and Steric Course at the Lithium-Bearing Terminus

Katsuhiko Tomooka, Nobuyuki Komine, Takeshi Nakai*
  • *Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan, Fax: +81-3-5734-2885; e-mail: takeshi@o.cc.titech.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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The [2,3]-Wittig rearrangement of an enantiomerically defined α-propargyloxy stannane with butyllithium is shown to proceed with complete inversion of configuration at the Li-bearing terminus. The periselectivity ([2,3]- vs. [1,2]-) of the rearrangement depends markedly upon the nature of substituents on the acetylenic group.

Wittig rearrangement - α-(propargyloxy)alkyllithiums - periselectivity - steric course - allenyl alcohol