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Enantioselective Construction of Tertiary C-O Bond via Allylic Substitution of Vinylethylene Carbonates with Water and Alcohols

Ajmal Khan, Sardaraz Khan, Ijaz Khan, Can Zhao, Yuxue Mao, Yan Chen and Yong Jian Zhang*

*School of Chemistry and Chemical Engineering, and Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China, Email: yjiansjtu.edu.cn

A. Khan, S. Khan, I. Khan, C. Zhao, Y. Mao, Y. Chen, Y. J. Zhang, J. Am. Chem. Soc., 2017, 139, 10733-10741.

DOI: 10.1021/jacs.7b04759 (free Supporting Information)


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Abstract

A cooperative catalysis system of an in situ generated chiral palladium complex and a boron reagent enables an enantioselective construction of tertiary C-O bond via asymmetric allylic substitution of racemic vinylethylene carbonates with water and alcohols. Valuable tertiary alcohols and ethers are obtained in high yields with complete regioselectivities and high enantioselectivities.

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Key Words

1,2-diols


ID: J48-Y2017