A chiroptical approach for the absolute stereochemical determination of P-stereogenic centers

Debarshi Chakraborty; Hadi Gholami; Aritra Sarkar; Leo A Joyce; James E Jackson; Babak Borhan

doi:10.1039/d0sc02940h

A chiroptical approach for the absolute stereochemical determination of P-stereogenic centers

Chem Sci. 2020 Dec 7;12(5):1750-1755. doi: 10.1039/d0sc02940h.

Authors

Debarshi Chakraborty¹, Hadi Gholami¹, Aritra Sarkar¹, Leo A Joyce², James E Jackson¹, Babak Borhan¹

Affiliations

¹ Michigan State University, Department of Chemistry East Lansing MI 48824 USA babak@chemistry.msu.edu.
² Department of Process Research and Development, Merck and Co, Inc. Rahway NJ 07065 USA.

Abstract

A simple chiroptical solution for the absolute stereochemical determination for asymmetric phosphorus V stereocenters is presented. Strong coordination of the phosphorus oxide with the Zn-metallo center of the racemic host Zn-MAPOL 2 leads to an induced axial chirality of the host, yielding a strong ECCD signal. A mnemonic is proposed to correlate the asymmetry of the guest molecule with the observed ECCD signal.