Stereospecific Si-C coupling and remote control of axial chirality by enantioselective palladium-catalyzed hydrosilylation of maleimides

Xing-Wei Gu, Yu-Li Sun, Jia-Le Xie, Xing-Ben Wang, Zheng Xu, Guan-Wu Yin, Li Li, Ke-Fang Yang and Li-Wen Xu ()
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Xing-Wei Gu: Hangzhou Normal University
Yu-Li Sun: Hangzhou Normal University
Jia-Le Xie: Hangzhou Normal University
Xing-Ben Wang: Hangzhou Normal University
Zheng Xu: Hangzhou Normal University
Guan-Wu Yin: Hangzhou Normal University
Li Li: Hangzhou Normal University
Ke-Fang Yang: Hangzhou Normal University
Li-Wen Xu: Hangzhou Normal University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: Abstract Hydrosilylation of unsaturated carbon-carbon bonds with hydrosilanes is a very important process to access organosilicon compounds and ranks as one of the most fundamental reactions in organic chemistry. However, catalytic asymmetric hydrosilylation of activated alkenes and internal alkenes has proven elusive, due to competing reduction of carbon-carbon double bond or isomerization processes. Herein, we report a highly enantioselective Si-C coupling by hydrosilylation of carbonyl-activated alkenes using a palladium catalyst with a chiral TADDOL-derived phosphoramidite ligand, which inhibits O-hydrosilylation/olefin reduction. The stereospecific Si-C coupling/hydrosilylation of maleimides affords a series of silyl succinimides with up to 99% yield, >99:1 diastereoselectivity and >99:1 enantioselectivity. The high degree of stereoselectivity exerts remote control of axial chirality, leading to functionalized, axially chiral succinimides which are versatile building blocks. The product utility is highlighted by the enantioselective construction of N-heterocycles bearing up to three stereocenters.

Date: 2020
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DOI: 10.1038/s41467-020-16716-5

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