American Chemical Society
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Metal Trifluoromethanesulfonate- Catalyzed Regioselective Borane-Reductive Ring Opening of Benzylidene Acetals:  A Concise Synthesis of 1,4-Dideoxy-1,4-imino-l-xylitol

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journal contribution
posted on 2002-02-06, 00:00 authored by Cheng-Chung Wang, Shun-Yuan Luo, Chi-Rung Shie, Shang-Cheng Hung
A highly regioselective borane-reductive ring opening of the 4,6-O-benzylidene-d-hexopyranosides to the corresponding 6-alcohols in excellent yields at room temperature via various metal trifluoromethanesulfonates as catalysts is described here. Its application in the synthesis of 1,4-dideoxy-1,4-imino-l-xylitol is also highlighted.