Enantioselective synthesis of 1-aryl tetrahydroisoquinolines by the rhodium-catalyzed reaction of 3,4-dihydroisoquinolinium tetraarylborates

Wei Sian Li, Ting Shen Kuo, Ping Yu Wu, Chien Tien Chen, Hsyueh Liang Wu

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The 1-aryl tetrahydroisoquinolines (1-aryl THIQs) are omnipresent in biologically active molecules. Here we report on the direct asymmetric synthesis of these valuable compounds via the reaction of 3,4-dihydroisoquinolinium tetraarylborates. The dual roles of anionic tetraarylborates, which function as both prenucleophiles and stabilizers of 3,4-dihydroisoquinolinium cations, enable this rhodium(I)-catalyzed protocol to convergently provide enantioenriched 1-aryl THIQs in good yields (≤95%) with ≤97% ee, as demonstrated by the formal synthesis of (−)-solifenacin and the facile synthesis of (−)-Cryptostyline I.

Original languageEnglish
Pages (from-to)1141-1146
Number of pages6
JournalOrganic Letters
Volume23
Issue number3
DOIs
Publication statusPublished - 2021 Feb 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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