3 years ago

Enantioselective Propargylation of Polyols and Desymmetrization of meso 1,2-Diols by Copper/Borinic Acid Dual Catalysis

Enantioselective Propargylation of Polyols and Desymmetrization of meso 1,2-Diols by Copper/Borinic Acid Dual Catalysis
Ren-Zhe Li, Hua Tang, Li-Qiang Wan, Xia Zhang, Ke R. Yang, Jie Liu, Zhengyan Fu, Dawen Niu
A copper/borinic acid dual catalytic reaction enabled the enantioselective propargylation of aliphatic polyols. Readily available reagents and catalysts were used in this transformation, which displayed good to excellent chemo- and stereoselectivity for a broad array of substrates. The method was also applicable to the desymmetrization of meso 1,2-diols to furnish products with three stereogenic centers and a terminal alkyne group in one operation. Together they're strong: A copper/borinic acid dual catalytic reaction was developed for the efficient and enantioselective propargylation of polyols. Control experiments revealed the essential role of each catalyst. The transformation is amenable to the desymmetrization of meso 1,2-diols to furnish compounds with three stereogenic centers in one step (see scheme).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703029

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