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Synlett 1996; 1996(3): 231-233
DOI: 10.1055/s-1996-5397
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A Novel Reducing System for Acetal Cleavage: BH3•S(CH3)2-BF3•O(C2H5)2 Combination

Seiki Saito* , Akiyoshi Kuroda, Kazuya Tanaka, Ryoichi Kimura
  • *Department of Bioengineering Science, Faculty of Engineering, Okayama University, Tsushima, Okayama 700, Japan
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Publikationsdatum:
31. Dezember 2000 (online)

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Acetals derived from 1,2- or 1,3-diols bearing neighboring hydroxyl group can be selectively cleaved at the acetal C-O bond proximate to the hydroxyl group on treatment initially with BH3⋅SMe2 for 1 h (0 °C-rt) and successfully with BF3⋅Et2O for 5 min at 0 °C.

acetal cleavage - benzilidene acetals - acetonides - BH3-BF3 combination - chemoselective reduction