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

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).