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Synlett 1991; 1991(2): 97-98
DOI: 10.1055/s-1991-20640
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Stereospecific Ring Opening at the Benzylic Carbon of Phenyloxirane Derivatives by Alcohols

Yoshihisa Niibo* , Tetsuya Nakata, Junzo Otera, Hitosi Nozaki
  • *Department of Applied Chemistry, Okayama University of Science, Ridai-cho, Okayama 700, Japan
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Publication Date:
07 March 2002 (online)

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Optically pure phenyl-substituted oxiranes underwent stereospecific ring opening at the benzylic position by benzyl alcohol and methanol with complete inversion under the catalysis of organotin phosphate condensates. With recourse to this reaction, a novel procedure for (S)-phenyloxirane was achieved from the readily available R counterpart via (S)-2-benzyloxy-2-phenylethanol.