Acylative Dynamic Kinetic Resolution of Secondary Alcohols: Tandem Catalysis by HyperBTM and Bäckvall's Ruthenium Complex

Journal of Organic Chemistry 2021
Artis Kinēns, S Balkaitis, O.K Ahmad, D.W Piotrowski, Edgars Sūna

Non-enzymatic dynamic kinetic resolution (DKR) of secondary alcohols by enantioselective acylation using an isothiourea-derived HyperBTM catalyst and racemization of slowly reacting alcohol by Bäckvall's ruthenium complex is reported. The DKR approach features high enantioselectivities (up to 99:1), employs easy-to-handle crystalline 4-nitrophenyl isobutyrate as the acylating reagent, and proceeds at room temperature and under an ambient atmosphere. The stereoinduction model featuring cation-πsystem interactions between the acylated HyperBTM catalyst and πelectrons of an alcohol aryl subunit has been elaborated by DFT calculations.

Atslēgas vārdi
Enantioselective Synthesis, Transfer Hydrogenation, Benzotetramisole, Derivatives, Selectivity
DOI
10.1021/acs.joc.1c00545
Hipersaite
https://pubs.acs.org/doi/10.1021/acs.joc.1c00545

Kinēns, A., Balkaitis, S., Ahmad, O., Piotrowski, D., Sūna, E. Acylative Dynamic Kinetic Resolution of Secondary Alcohols: Tandem Catalysis by HyperBTM and Bäckvall's Ruthenium Complex. Journal of Organic Chemistry, 2021, Vol. 86, No. 10, 7189.-7202.lpp. ISSN 0022-3263. e-ISSN 1520-6904. Pieejams: doi:10.1021/acs.joc.1c00545

Publikācijas valoda
English (en)