Catalytic enantioselective conjugate reduction of lactones and lactams.
A dramatic acceleration of the enantioselective copper-catalyzed conjugate reduction of alpha,beta-unsaturated lactones, lactams, and esters is reported upon addition of alcohol additives. Good to excellent yields and enantioselectivities were realized using a catalyst generated in situ from CuCl(2).H(2)O, t-BuONa, p-tol-BINAP, and PMHS, and this methodology was applied to the synthesis of (-)-Paroxetine.
Hughes
Gregory
G
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Kimura
Masanari
M
Buchwald
Stephen L
SL
D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D007769:Lactams / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D017374:Paroxetine / Q000138:chemical synthesis* / Q000737:chemistry*
D000438:Alcohols; D007769:Lactams; D007783:Lactones; D017374:Paroxetine