Download PDF
Synfacts 2011(9): 0989-0989  
DOI: 10.1055/s-0030-1261005
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-Keto-anti-1,3-Diols by Chemoselective Tandem Oxidation

Contributor(s): Mark Lautens, Hasnain A. Malik
M. M. Hussain, J. H. Toribio, P. J. Carroll, P. J. Walsh*
University of Pennsylvania, Philadelphia, USA
Further Information

Publication History

Publication Date:
19 August 2011 (online)

    Permissions and Reprints

Significance

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).