Catalytic Asymmetric Cascade Dearomatization of Indoles via a Photoinduced Pd‐Catalyzed 1,2‐Bisfunctionalization of Butadienes

Author:

Zhan Xiaohang1,Nie Zhiwen1,Li Na2,Zhou Ao1,Lv Haotian1,Liang Mingrong1,Wu Keqin1,Cheng Gui‐Juan2,Yin Qin1ORCID

Affiliation:

1. Shenzhen University of Advanced Technology, and Shenzhen Institute of Advanced Technology Chinese Academy of Sciences 518055 Shenzhen P. R. China

2. Warshel Institute for Computational Biology School of Medicine The Chinese University of Hong Kong 518172 Shenzhen Guangdong P. R. China

Abstract

AbstractPhotoinduced Pd‐catalyzed bisfunctionalization of butadienes with a readily available organic halide and a nucleophile represents an emerging and attractive method to assemble versatile alkenes bearing various functional groups at the allylic position. However, enantiocontrol and/or diastereocontrol in the C−C or C−X bond‐formation step have not been solved due to the open‐shell process. Herein, we present a cascade asymmetric dearomatization reaction of indoles via photoexcited Pd‐catalyzed 1,2‐biscarbonfunctionalization of 1,3‐butadienes, wherein asymmetric control on both the nucleophile and electrophile part is achieved for the first time in photoinduced bisfunctionalization of butadienes. This method delivers structurally novel chiral spiroindolenines bearing two contiguous stereogenic centers with high diastereomeric ratios (up to >20 : 1 dr) and good to excellent enantiomeric ratios (up to 97 : 3 er). Experimental and computational studies of the mechanism have confirmed a radical pathway involving excited‐state palladium catalysis. The alignment and non‐covalent interactions between the substrate and the catalyst were found to be essential for stereocontrol.

Publisher

Wiley

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