Direct access of the chiral quinolinyl core of cinchona alkaloids via a brønsted acid and chiral amine co-catalyzed chemo- and enantioselective α-alkylation of quinolinylmethanols with enals

Mengchao Tong, Sinan Wang, Jinchen Zhuang, Cong Qin, Hao Li, Wei Wang

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

A strategy for the facile construction of the chiral quinolinylmethanolic structure, a core featured in cinchona alkaloids, is reported. A new reactivity is harnessed by TfOH-promoted chemoselective activation of α-C-H over O-H bond in quinolinylmethanols. The new reactivity is successfully engineered with an iminium catalysis in a synergistic manner to create a powerful conjugate addition-cyclization cascade process for synthesis of chiral quinoline derived π-butyrolactones in good yields and with good to excellent enantioselectivities. The method enables the first total synthesis of natural product broussonetine in three steps.

Original languageEnglish (US)
Pages (from-to)1195-1199
Number of pages5
JournalOrganic Letters
Volume20
Issue number4
DOIs
StatePublished - Feb 16 2018
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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