Issue 9, 2021

Organocatalytic 1,6-hydrophosphination of para-quinone methides: enantioselective access to chiral 3-phosphoxindoles bearing phosphorus-substituted quaternary carbon stereocenters

Abstract

An efficient organocatalytic enantioselective 1,6-hydrophosphonylation of para-quinone methides derived from isatins with H-phosphorus oxides has been achieved in the presence of bifunctional cinchona alkaloid-based urea. This methodology provides a straightforward approach for accessing a variety of chiral 3-phosphoxindoles bearing phosphorus-substituted quaternary carbon stereocenters with a high level of chemoselectivity and remote stereocontrol (up to 99% yield, 99 : 1 er). This environmentally benign protocol represents a unique example of the asymmetric organocatalytic 1,6-conjugate addition reaction of phosphorus nucleophiles in an atom-economical manner.

Graphical abstract: Organocatalytic 1,6-hydrophosphination of para-quinone methides: enantioselective access to chiral 3-phosphoxindoles bearing phosphorus-substituted quaternary carbon stereocenters

Supplementary files

Article information

Article type
Research Article
Submitted
27 Dec 2020
Accepted
01 Mar 2021
First published
01 Mar 2021

Org. Chem. Front., 2021,8, 2002-2008

Organocatalytic 1,6-hydrophosphination of para-quinone methides: enantioselective access to chiral 3-phosphoxindoles bearing phosphorus-substituted quaternary carbon stereocenters

L. Wang, F. Yang, X. Xu and J. Jiang, Org. Chem. Front., 2021, 8, 2002 DOI: 10.1039/D0QO01638A

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