Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation

Cai You, Xiuxiu Li, Yuhong Yang, Yu-Sheng Yang, Xuefeng Tan, Shuailong Li, Biao Wei, Hui Lv (), Lung-Wa Chung () and Xumu Zhang ()
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Cai You: Wuhan University
Xiuxiu Li: Wuhan University
Yuhong Yang: Southern University of Science and Technology, Shenzhen
Yu-Sheng Yang: Wuhan University
Xuefeng Tan: Southern University of Science and Technology, Shenzhen
Shuailong Li: Wuhan University
Biao Wei: Wuhan University
Hui Lv: Wuhan University
Lung-Wa Chung: Southern University of Science and Technology, Shenzhen
Xumu Zhang: Wuhan University

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract Hydroformylation of 1,2-disubstituted alkenes usually occurs at the α position of the directing heteroatom such as oxygen atom and nitrogen atom. By contrast, to achieve hydroformylation on the β position of the heteroatom is a tough task. Herein, we report the asymmetric rhodium-catalyzed hydroformylation of 1,2-disubstituted alkenylsilanes with excellent regioselectivity at the β position (relative to the silicon heteroatom) and enantioselectivity. In a synthetic sense, we achieve the asymmetric hydroformylation on the β position of the oxygen atom indirectly by using the silicon group as a surrogate for the hydroxyl. Density functional theory (DFT) calculations are carried out to examine energetics of the whole reaction path for Rh/YanPhos-catalyzed asymmetric hydroformylation and understand its regioselectivity and enantioselectivity. Our computational study suggests that the silicon group can activate the substrate and is critical for the regioselectivity.

Date: 2018
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DOI: 10.1038/s41467-018-04277-7

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