Issue 11, 2018

Tailored trisubstituted chiral CpxRhIII catalysts for kinetic resolutions of phosphinic amides

Abstract

A trisubstituted chiral Cpx ligand family is introduced. Based on the disubstituted atropchiral Cpx ligand scaffold, the introduction of a bulky third substituent at the central position of the Cp ring leads to substantially increased selectivities for rhodium(III)-catalyzed kinetic resolutions and allowed for s-factors of up to 50. Their superiority is demonstrated by kinetic resolutions of phosphinic amides providing access to compounds with stereogenic phosphorus(V) atoms. The unreacted acyclic phosphinic amide and the cyclized product are both obtained in good yields and enantioselectivities. The ligand synthesis capitalizes on a late stage modification and expands the accessible ligand Cpx ligand portfolio.

Graphical abstract: Tailored trisubstituted chiral CpxRhIII catalysts for kinetic resolutions of phosphinic amides

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Dez 2017
Accepted
03 Feb 2018
First published
05 Feb 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 2981-2985

Tailored trisubstituted chiral CpxRhIII catalysts for kinetic resolutions of phosphinic amides

Y. Sun and N. Cramer, Chem. Sci., 2018, 9, 2981 DOI: 10.1039/C7SC05411D

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