An organocatalytic cascade approach toward polysubstituted quinolines and chiral 1,4-dihydroquinolines-unanticipated effect of N-protecting groups

Xinshuai Zhang, Xixi Song, Hao Li, Shilei Zhang, Xiaobei Chen, Xinhong Yu, Wei Wang

Research output: Contribution to journalArticlepeer-review

74 Scopus citations

Abstract

A matter of protection: The outcome of a divergent organocatalytic aza-Michael/aldol cascade process toward quinolines and 1,4-dihydroquinolines depends on the choice of the N-protecting group (see scheme; TEA=triethylamine, TMS=trimethylsilyl). Use of an electron-donating sulfonyl group results in an unanticipated aza-Michael/aldol/aromatization cascade to give polysubstituted quinolines (right). In contrast, chiral 1,4-dihydroquinolines are obtained with an electron-withdrawing sulfonyl group (left).

Original languageEnglish (US)
Pages (from-to)7282-7286
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number29
DOIs
StatePublished - Jul 16 2012
Externally publishedYes

Keywords

  • 1,4-dihydroquinolines
  • Cascade reactions
  • Divergent synthesis
  • Organocatalysis
  • Quinolines

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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