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Synlett 1998; 1998(12): 1429-1431
DOI: 10.1055/s-1998-1978
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Enantioselective [2,3]-Wittig Rearrangement via Sparteine-Mediated Lateral Metalation of N,N-Dialkyl-o-allyloxymethylbenzamides and o-Substituted Benzyl Prenyl Ethers

Takeshi Kawasaki* , Tetsutaro Kimachi
  • *Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8304, Japan; Fax + 81 75 761 2689; E-mail: tkimachi@pharmsun.pharm.kyoto-u.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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The (-)-sparteine-mediated enantioselective [2,3]-Wittig rearrangement of N,N-dialkyl-o-allyloxymethylbenzamides and o-substituted benzyl prenyl ethers has been investigated. With N,N-diethyl-o-allyloxymethylbenzamide, enantiomeric excess up to 60% was observed in pentane. These results suggest that the carbamoyl group can effectively assist the transfer of stereoinformation by coordinating with the (-)-sparteine-n-BuLi complex. Other functional groups (OMe, OCONR2, OMOM, F) were impotent to the enantiodifferentiation of this rearrangement.

[2,3]-Wittig rearrangement - (-)-sparteine - benzyl prenyl ether - lateral metalation