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

Journal Article


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.

Publication Date


  • 2017

Citation


  • Hong, S. N., Liu, Y., Lee, R., & Jiang, Z. (2017). Asymmetric tandem conjugate addition-protonation to forge chiral secondary C-O bonds for quaternary carbon stereocenters at the nonadjacent β-position. Chemical Communications, 53(54), 7493-7496. doi:10.1039/c7cc03700g

Scopus Eid


  • 2-s2.0-85021950265

Start Page


  • 7493

End Page


  • 7496

Volume


  • 53

Issue


  • 54

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.

Publication Date


  • 2017

Citation


  • Hong, S. N., Liu, Y., Lee, R., & Jiang, Z. (2017). Asymmetric tandem conjugate addition-protonation to forge chiral secondary C-O bonds for quaternary carbon stereocenters at the nonadjacent β-position. Chemical Communications, 53(54), 7493-7496. doi:10.1039/c7cc03700g

Scopus Eid


  • 2-s2.0-85021950265

Start Page


  • 7493

End Page


  • 7496

Volume


  • 53

Issue


  • 54