title: Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters.
abstract: A highly enantioselective transformation catalyzed by chiral (acyclic diaminocarbene)gold(I) complexes is reported. The enantioselective synthesis of 2-substituted chromenyl pivalates from racemic phenol-substituted propargyl pivalates was developed. Rearrangement of the substrates in the presence of cationic gold gave allene intermediates, whose cyclization resulted in formation of enantioenriched product through a dynamic kinetic asymmetric transformation.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Yi-Ming
authors.initials: YM
authors.lastname: Wang
authors.forename: Christian N
authors.initials: CN
authors.lastname: Kuzniewski
authors.forename: Vivek
authors.initials: V
authors.lastname: Rauniyar
authors.forename: Christina
authors.initials: C
authors.lastname: Hoong
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D006046:Gold; D008697:Methane / Q000031:analogs & derivatives; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D004952:Esters; C030011:carbene; D006046:Gold; D008697:Methane