Metal trifluoromethanesulfonate-catalyzed regioselective borane-reductive ring opening of benzylidene acetals: a concise synthesis of 1,4-dideoxy-1,4-imino-L-xylitol.

Cheng-Chung Wang, Shun-Yuan Luo, Chi-Rung Shie, Shang-Cheng Hung

Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan.

Organic letters 2002 Mar 7

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reaction: see text] 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.

Citation

Cheng-Chung Wang, Shun-Yuan Luo, Chi-Rung Shie, Shang-Cheng Hung. Metal trifluoromethanesulfonate-catalyzed regioselective borane-reductive ring opening of benzylidene acetals: a concise synthesis of 1,4-dideoxy-1,4-imino-L-xylitol. Organic letters. 2002 Mar 7;4(5):847-9