Jump to main content
Jump to site search


Asymmetric tandem conjugate addition–protonation to forge chiral secondary C–O bonds for quaternary carbon stereocenters at the nonadjacent β-position

Author affiliations

Abstract

A direct strategy to construct chiral secondary C–O bonds for quaternary carbon stereocenters at the nonadjacent β-position is described. Methylene 1,3-oxazolidine-2,4-diones were for the first time employed in an asymmetric reaction as viable electrophiles undergoing a tandem conjugate addition–protonation process. Using an L-amino acid-based urea–tertiary amine catalyst, the reaction with 3-substituted oxindoles gave valuable protonation adducts featuring 1,3-quaternary–tertiary (C–O) nonadjacent stereocenters in high yields and excellent stereoselectivities. The method was successfully extended to sulphur nucleophiles for synthesizing chiral 1,3-sulfur-tertiary alcohol derivatives with bioactive importance.

Graphical abstract: Asymmetric tandem conjugate addition–protonation to forge chiral secondary C–O bonds for quaternary carbon stereocenters at the nonadjacent β-position

Back to tab navigation

Supplementary files

Publication details

The article was received on 12 May 2017, accepted on 13 Jun 2017 and first published on 13 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC03700G
Citation: Chem. Commun., 2017, Advance Article
  •   Request permissions

    Asymmetric tandem conjugate addition–protonation to forge chiral secondary C–O bonds for quaternary carbon stereocenters at the nonadjacent β-position

    S. Hong, Y. Liu, R. Lee and Z. Jiang, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC03700G

Search articles by author

Spotlight

Advertisements