A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction.
A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.
Evans
David A
DA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. evans@chemistry.harvard.edu
Seidel
Daniel
D
Rueping
Magnus
M
Lam
Hon Wai
HW
Shaw
Jared T
JT
Downey
C Wade
CW
D000085:Acetates / Q000737:chemistry; D000438:Alcohols / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis*; D009595:Nitroparaffins / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D000438:Alcohols; D009574:Nitro Compounds; D009595:Nitroparaffins; D009942:Organometallic Compounds; D010080:Oxazoles; D003300:Copper; D008697:Methane; C008640:nitromethane