Merging nucleophilic and hydrogen bonding catalysis: an anion binding approach to the kinetic resolution of propargylic amines.
An efficient kinetic resolution of primary propargylic amines with s-factors of up to 56 is reported. The strategy is based on a dual catalytic approach, namely the use of a newly developed and easy-to-make thiourea-amide anion binding catalyst in combination with 4-(dimethylamino)pyridine (DMAP), both employed at a 5 mol % catalyst loading. Benzylic amines are also resolved with s-factors of up to 38.
Klauber
Eric G
EG
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, USA.
De
Chandra Kanta
CK
Shah
Tejas K
TK
Seidel
Daniel
D
D015761:4-Aminopyridine / Q000031:analogs & derivatives / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D001665:Binding Sites; D002384:Catalysis; D006860:Hydrogen Bonding; D007700:Kinetics; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000577:Amides; D000838:Anions; D011437:Propylamines; C009054:propargylamine; D010293:Pargyline; D015761:4-Aminopyridine; D013890:Thiourea; C003885:4-dimethylaminopyridine