Rhodium-catalyzed intermolecular enantioselective Alder–ene type reaction of cyclopentenes with silylacetylenes

Dongquan Zhang, Miaomiao Li, Jiajia Li, Aijun Lin () and Hequan Yao ()
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Dongquan Zhang: China Pharmaceutical University
Miaomiao Li: China Pharmaceutical University
Jiajia Li: China Pharmaceutical University
Aijun Lin: China Pharmaceutical University
Hequan Yao: China Pharmaceutical University

Nature Communications, 2021, vol. 12, issue 1, 1-7

Abstract: Abstract The Alder–ene type reaction between alkenes and alkynes provides an efficient and atom-economic method for the construction of C-C bond, which has been widely employed in the synthesis of natural products and other functional molecules. The intramolecular enantioselective Alder-ene cycloisomerization reactions of 1,n-enynes have been extensively investigated. However, the intermolecular asymmetric version has not been reported, and remains a challenging task. Herein, we describe a rhodium-catalyzed intermolecular enantioselective Alder-ene type reaction of cyclopentenes with silylacetylenes. A variety of chiral (E)-vinylsilane tethered cyclopentenes bearing one quaternary carbon and one tertiary carbon stereocenters are achieved in high yields and enantioselectivities. The reaction undergoes carbonyl-directed migratory insertion, β-H elimination and desymmetrization of prochiral cyclopentenes processes.

Date: 2021
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DOI: 10.1038/s41467-021-26955-9

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