0000000000814753
AUTHOR
David W. Piotrowski
Development of a Chiral DMAP Catalyst for the Dynamic Kinetic Resolution of Azole Hemiaminals
A new catalyst for the dynamic kinetic resolution of azole hemiaminals has been developed using late-stage structural modifications of the tert-leucinol-derived chiral subunit of DMAP species.
Acylative Dynamic Kinetic Resolution of Secondary Alcohols: Tandem Catalysis by HyperBTM and Bäckvall's Ruthenium Complex.
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 Backvall'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-π system interactions between the acylated HyperBTM catalyst and π electrons of an alcohol aryl subunit has been elaborated by DFT calculations.
CCDC 1528810: Experimental Crystal Structure Determination
Related Article: Artis Kinens, Marcis Sejejs, Adam S. Kamlet, David W. Piotrowski, Edwin Vedejs, Edgars Suna|2017|J.Org.Chem.|82|869|doi:10.1021/acs.joc.6b02955
CCDC 1528809: Experimental Crystal Structure Determination
Related Article: Artis Kinens, Marcis Sejejs, Adam S. Kamlet, David W. Piotrowski, Edwin Vedejs, Edgars Suna|2017|J.Org.Chem.|82|869|doi:10.1021/acs.joc.6b02955