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Synlett 1993; 1993(2): 127-129
DOI: 10.1055/s-1993-22373
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Reductive Cleavage of Chiral Acetals Using New Aluminum Catalyst

Kazuaki Ishihara* , Naoyuki Hanaki, Hisashi Yamamoto
  • *Department of Applied Chemistry, Faculty of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, Aichi, 464-01, Japan
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Publication Date:
19 March 2002 (online)

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The reaction of acetals derived from (-)-(2R,4R)-2,4-pentanediol and ketones in the presence of a catalytic amount of aluminum pentafluorophenoxide produces reductively cleaved products with high diastereoselectivity. The reaction is a new method for diastereoselective cleavage of acetals: an intramolecular Meerwein-Ponndorf-Verley reductive and Oppenauer oxidative reaction on an acetal template.