Highly Selective and Catalytic Generation of Acyclic Quaternary Carbon Stereocenters via Functionalization of 1,3-Dienes with CO₂

Xiao-Wang Chen, Lei Zhu, Yong-Yuan Gui, Ke Jing, Yuan-Xu Jiang, Zhi-Yu Bo, Yu Lan*, Jing Li and Da-Gang Yu*

*School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030; College of Chemistry, Sichuan University, Chengdu 610064, P. R. China; Email: lanyucqu.edu.cn, dgyuscu.edu.cn

X.-W. Chen, L. Zhu, Y.-Y. Gui, K. Jing, Y.-X. Jiang, Z.-Y. Bo, Y. Lan, J. Li, D.-G. Yu, J. Am. Chem. Soc., 2019, 141, 18825-18835.

DOI: 10.1021/jacs.9b09721

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Abstract

A highly selective copper-catalyzed reductive hydroxymethylation of 1,3-dienes with CO₂ provides chiral all-carbon acyclic quaternary stereocenters. A variety of readily available 1,1-disubstituted 1,3-dienes, as well as a 1,3,5-triene, undergo the reaction with high chemo-, regio-, E/Z-, and enantioselectivities and good functional group tolerance.

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Key Words

homoallylic alcohols, dimethoxymethylsilane

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ID: J48-Y2019