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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, Email:

N. Bajwa, M. P. Jennings, J. Org. Chem., 2008, 73, 3638-3641.

DOI: 10.1021/jo800150x

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Red-Al is an efficient chelation-controlled reducing reagent for acyclic acetal-protected R-hydroxy ketones. Typically, high diastereomeric ratios and yields can be achieved for the synthesis of 1,2-anti-diols.

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Key Words

Red-Al, Reduction of Carbonyl Compounds, Methoxymethyl Ethers

ID: J42-Y2008-1260