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Synthesis of 2-Keto-anti-1,3-Diols by Chemoselective Tandem Oxidation
M. M. Hussain, J. H. Toribio, P. J. Carroll, P. J. Walsh*
University of Pennsylvania, Philadelphia, USA
19 August 2011 (online)
The authors disclose a stereoselective approach to the synthesis of 2-keto-anti-1,3-diols. Their approach involves a tandem oxidation of readily available 2-B(pin)-substituted allylic alcohols. The importance of 2-keto-1,3-diols is exemplified by their abundance in polyoxygenated hydrocarbons in nature. The authors build on their previous work [vinyl zinc additions to aldehydes to form B(pin)-substituted allylic alcohols] to further highlight the utility of their allylic alcohol products. Yields are generally moderate to excellent and diastereoselectivities are excellent (dr > 20:1).