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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)1481-1485
Number of pages5
JournalOrganic Letters
Volume24
Issue number7
DOIs
Publication statusPublished - 2022 Feb 25

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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