Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy

Yu-Han Nie; Masaaki Komatsuda; Ping Yang; Chao Zheng; Junichiro Yamaguchi; Shu-Li You

doi:10.1021/acs.orglett.2c00129

Pd-Catalyzed Asymmetric Dearomative Arylation of Indoles via a Desymmetrization Strategy

Org Lett. 2022 Feb 25;24(7):1481-1485. doi: 10.1021/acs.orglett.2c00129. Epub 2022 Feb 14.

Authors

Yu-Han Nie^{1

2}, Masaaki Komatsuda³, Ping Yang², Chao Zheng², Junichiro Yamaguchi³, Shu-Li You^{1

2}

Affiliations

¹ Chang-Kung Chuang Institute, East China Normal University, Shanghai 200062, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
³ Department of Applied Chemistry, Waseda University, 513 Wasedatsurumakicho, Shinjuku, Tokyo 162-0041, Japan.

PMID: 35156828
DOI: 10.1021/acs.orglett.2c00129

Abstract

Pd-catalyzed asymmetric dearomative arylation of C3-substituted indoles is realized via a desymmetrization strategy. A BINOL-derived chiral phosphoramidite ligand is found to be highly efficient for the stereoselective control in this reaction. This method provides a convenient synthesis of spiroindolenines bearing two stereogenic centers in good yields (up to 98%) with excellent diastereo- and enantioselectivities (up to >20:1 dr and 97% ee), which could also be applied in asymmetric dearomative arylation of the simple C3-tethered indoles.