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Synlett 1998; 1998(12): 1353-1354
DOI: 10.1055/s-1998-1992
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Stereospecific Nucleophilic Substitution of Optically Active 1-Benzyloxy-2,2,2-trifluoroethyl Tosylate with Lithium Tetraalkylaluminates Prepared by the Ti-Catalyzed Hydroalumination of Olefins

Hiroshi Matsutani* , Hervé Poras, Tetsuo Kusumoto, Tamejiro Hiyama
  • *Sagami Chemical Research Center, Nishiohnuma 4-4-1, Sagamihara, Kanagawa 229-0012, Japan; Fax + 81-427-49-7631; E-mail: kus-scrc@bekkoame.ne.jp
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Publication Date:
31 December 2000 (online)

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Reaction of optically active 1-benzyloxy-2,2,2-trifluoroethyl tosylate with lithium tetraalkylaluminates prepared by the Cp2TiCl2-catalyzed hydroalumination of olefins with LiAlH4 gives optically active 1-alkyl-2,2,2-trifluoroethyl benzyl ethers with inversion of configuration.

acetals - aluminum reagents - fluorinated compounds - nucleophilic substitution - stereospecificity