Switchable organocatalytic enantioselective sulfenocyclization of cyclohexadienes enabling chemodivergent access to chiral bicyclo[m.n.1] ring systems

Bing-Qian Zhang, Lei Chen, Wen-Ying Xiao, Yidong Liu (), Yin-Long Li () and Jun Deng ()
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Bing-Qian Zhang: Chongqing University
Lei Chen: Chongqing University
Wen-Ying Xiao: Chongqing University
Yidong Liu: Chongqing University
Yin-Long Li: 1364 Clifton Rd
Jun Deng: Chongqing University

Nature Communications, 2025, vol. 16, issue 1, 1-10

Abstract: Abstract The precise control over regio- and stereoselectivity from the same substrate represents a significant challenge in organic chemistry. Herein, a switchable organocatalytic enantioselective carbosulfenylation/sulfenolactonization of cyclohexa-1,4-dienes to access the chiral bicyclo[m.n.1] ring systems, which are the critical core skeleton of many important natural products and biologically active compounds, is achieved. By simply tuning the substituent of the sulfenylating agent, a series of synthetically challenging chiral bridged bicyclo[3.3.1]nonanes and 2-oxabicyclo[3.2.1]octanes bearing three consecutive stereocenters are obtained with good yields and excellent enantioselectivities (up to 94% yield and 97% ee). Furthermore, the initial investigation of the bicyclic derivative as a chiral ligand in metal catalysis is also conducted. Our findings offer a version of switchable divergent asymmetric synthesis in which different products can be controllably generated from an identical set of substrates by simply adjusting reaction parameters.

Date: 2025
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DOI: 10.1038/s41467-025-59918-5

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