Fluxionally chiral DMAP catalysts: kinetic resolution of axially chiral biaryl compounds

Gaoyuan Ma; Jun Deng; Mukund P Sibi

doi:10.1002/anie.201406684

Fluxionally chiral DMAP catalysts: kinetic resolution of axially chiral biaryl compounds

Angew Chem Int Ed Engl. 2014 Oct 27;53(44):11818-21. doi: 10.1002/anie.201406684. Epub 2014 Aug 14.

Authors

Gaoyuan Ma¹, Jun Deng, Mukund P Sibi

Affiliation

¹ Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND 58108 (USA).

PMID: 25124842
DOI: 10.1002/anie.201406684

Abstract

Can organocatalysts that incorporate fluxional groups provide enhanced selectivity in asymmetric transformations? To address this issue, we have designed chiral 4-dimethylaminopyridine (DMAP) catalysts with fluxional chirality. These catalysts were found to be efficient in promoting the acylative kinetic resolution of secondary alcohols and axially chiral biaryl compounds with selectivity factors of up to 37 and 51, respectively.

Keywords: acylation; biaryls; fluxionality; kinetic resolution; organocatalysis.