Copper-catalyzed asymmetric conjugate reduction as a route to novel beta-azaheterocyclic acid derivatives.
A chiral copper-hydride catalyst for the asymmetric conjugate reduction of alpha,beta-unsaturated carbonyl compounds has been used for the reduction of substrates containing beta-nitrogen substituents. A new set of reaction conditions has allowed for a variety of beta-azaheterocyclic acid derivatives to be synthesized in excellent yields and with high degrees of enantioselectivity. In addition, the effect that the nature of the nitrogen substituent has on the rate of the conjugate reduction reaction has been explored.
Rainka
Matthew P
MP
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Aye
Yimon
Y
Buchwald
Stephen L
SL
D000143:Acids / Q000138:chemical synthesis; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*
D000143:Acids; D006571:Heterocyclic Compounds; D003300:Copper