Photocatalytic Z/E isomerization unlocking the stereodivergent construction of axially chiral alkene frameworks

Jie Wang, Jun Gu, Jia-Yu Zou, Meng-Jie Zhang, Rui Shen, Zhiwen Ye, Ping-Xun Xu and Ying He ()
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Jie Wang: Nanjing University of Science and Technology
Jun Gu: Nanjing University of Science and Technology
Jia-Yu Zou: Nanjing University of Science and Technology
Meng-Jie Zhang: Nanjing University of Science and Technology
Rui Shen: Nanjing University of Science and Technology
Zhiwen Ye: Nanjing University of Science and Technology
Ping-Xun Xu: Nanjing University of Science and Technology
Ying He: Nanjing University of Science and Technology

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: Abstract The past century has witnessed a large number of reports on the Z/E isomerization of alkenes. However, the vast majority of them are still limited to the isomerization of di- and tri-substituted alkenes. The stereospecific Z/E isomerization of tetrasubstituted alkenes remains to be an underdeveloped area, thus lacking in a stereodivergent synthesis of axially chiral alkenes. Herein we report the atroposelective synthesis of tetrasubstituted alkene analogues by asymmetric allylic substitution-isomerization, followed by their Z/E isomerization via triplet energy transfer photocatalysis. In this regard, the stereodivergent synthesis of axially chiral N-vinylquinolinones is achieved efficiently. Mechanistic studies indicate that the benzylic radical generation and distribution are two key factors for preserving the enantioselectivities of axially chiral compounds.

Date: 2024
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DOI: 10.1038/s41467-024-47404-3

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