Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.
The gold-catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer.
Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
Dimitri A
DA
Khrakovsky
Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.|School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang, 222005, P.R. China.
Chuanzhou
C
Tao
Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.|Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA, 91125, USA.
Miles W
MW
Johnson
Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
Richard T
RT
Thornbury
Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
Sophia L
SL
Shevick
Department of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA. fdtoste@berkeley.edu.
F Dean
FD
Toste
D000466:Alkadienes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D000588:Amines; D056831:Coordination Complexes; C030011:carbene; D006046:Gold; D008697:Methane
acyclic diaminocarbene; enantioselective synthesis; gold catalysis; hydroamination; hydroazidation