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

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-pro...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017-07, Vol.53 (54), p.7493-7496
Main Authors: Hong, San-Ni, Liu, Yang, Lee, Richmond, Jiang, Zhiyong
Format: Article
Language:English
Subjects:
Asymmetry
Carbon
Chemical bonds
Conjugates
Derivatives
Methylene
Stereoselectivity
Sulfur
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc03700g