An Efficient 1,2-Chelation-Controlled Reduction of Protected Hydroxy Ketones via Red-Al

Naval Bajwa and Michael P. Jennings
Department of Chemistry, 250 Hackberry Lane, The University of Alabama, Tuscaloosa, Alabama 35487-0336
J. Org. Chem., 2008, 73 (9), pp 3638–3641
DOI: 10.1021/jo800150x
Publication Date (Web): March 22, 2008
Copyright © 2008 American Chemical Society

Abstract

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In this paper, we have demonstrated that Red-Al is an efficient chelation-controlled reducing reagent for acyclic acetal (i.e., MOM, MEM, SEM, and BOM) protected α-hydroxy ketones. Typically, diastereomeric ratios (dr) ranged from 5 to 20:1 for the 1,2-anti-diols in good to excellent yields.

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    History

    • Published In Issue May 02, 2008
    • Article ASAPMarch 22, 2008
    • Received: January 21, 2008

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