Catalytic asymmetric C–Si bond activation via torsional strain-promoted Rh-catalyzed aryl-Narasaka acylation

Jia Feng, Xiufen Bi, Xiaoping Xue, Na Li, Lei Shi and Zhenhua Gu ()
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Jia Feng: University of Science and Technology of China
Xiufen Bi: University of Science and Technology of China
Xiaoping Xue: University of Science and Technology of China
Na Li: University of Science and Technology of China
Lei Shi: University of Science and Technology of China
Zhenhua Gu: University of Science and Technology of China

Nature Communications, 2020, vol. 11, issue 1, 1-12

Abstract: Abstract Atropisomers are important organic frameworks in bioactive natural products, drugs as well as chiral catalysts. Meanwhile, silanols display unique properties compared to their alcohol analogs, however, the catalytic synthesis of atropisomers bearing silanol groups is challenging. Here, we show a rhodium-catalyzed torsional strain-promoted asymmetric ring-opening reaction for the synthesis of α-silyl biaryl atropisomers. The reaction features a dynamic kinetic resolution of C(Ar)-Si bond cleavage, whose stereochemistry was controlled by a phosphoramidite ligand derived from (S)-3-methyl-1-((2,4,6-triisopropylphenyl)sulfonyl)piperazine. This work is a demonstration of an aryl-Narasaka acylation, where the C(Ar)-Si bond cleavage is promoted by the torsional strain of α, α’-disubstituted silafluorene.

Date: 2020
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DOI: 10.1038/s41467-020-18273-3

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