Stereoselective intermolecular radical cascade reactions of tryptophans or ɤ-alkenyl-α-amino acids with acrylamides via photoredox catalysis

Jiang-Tao Li, Jian-Nan Luo, Jia-Le Wang, Wang De-Ku, Yi-Zhe Yu and Chun-Xiang Zhuo ()
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Jiang-Tao Li: College of Chemistry and Chemical Engineering, Xiamen University
Jian-Nan Luo: College of Chemistry and Chemical Engineering, Xiamen University
Jia-Le Wang: College of Chemistry and Chemical Engineering, Xiamen University
Wang De-Ku: College of Chemistry and Chemical Engineering, Xiamen University
Yi-Zhe Yu: College of Chemistry and Chemical Engineering, Xiamen University
Chun-Xiang Zhuo: College of Chemistry and Chemical Engineering, Xiamen University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract The radical cascade reaction is considered as one of the most powerful methods to build molecular complexity. However, highly stereoselective intermolecular radical cascade reactions that can produce complex cyclic compounds bearing multiple stereocenters via visible-light-induced photocatalysis have been challenging yet desirable. Herein we report a facile and efficient synthesis of multi-substituted trans-fused hexahydrocarbazoles via a stereoselective intermolecular radical cascade reaction of readily available tryptophans and acrylamides enabled by visible-light-induced photoredox catalysis. The trans-fused hexahydrocarbazoles with up to five stereocenters including two quaternary ones can be accessed in up to 82% yield, >20/1 diastereoselectivity, and 96% ee. Interestingly, the tetrahydrocarbazoles are favorably formed when the reaction is performed under air. Moreover, by simply switching the starting material from tryptophans to ɤ-alkenyl substituted α-amino acids, this protocol can be further applied to the stereoselective syntheses of 1,3,5-trisubstituted cyclohexanes which are otherwise challenging to access. Preliminary mechanistic studies suggest that the reaction goes through radical addition cascade and radical-polar crossover processes.

Date: 2022
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DOI: 10.1038/s41467-022-29464-5

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