The catalytic enantioselective synthesis of tetrahydroquinolines containing all-carbon quaternary stereocenters via the formation of aza-ortho-xylylene with 1,2-dihydroquinoline as a precursor

Chem Commun (Camb). 2016 Feb 7;52(11):2304-6. doi: 10.1039/c5cc07752d.

Abstract

Tetrahydroquinolines () with an all-carbon quaternary stereocenter were effectively obtained via the in situ formation of aza-ortho-xylylene () with easily accessible 1,2-dihydroquinolines as precursors. The reaction was rationalized with chiral phosporic acid to afford chiral with high yield and excellent enantioselectivity.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Carbon / chemistry*
  • Catalysis
  • Quinolones / chemical synthesis*
  • Quinolones / chemistry
  • Stereoisomerism

Substances

  • Quinolones
  • Carbon