Cu(I)-catalyzed reductive aldol cyclizations: diastereo- and enantioselective synthesis of beta-hydroxylactones.
[reaction: see text] Copper bisphosphine complexes catalyze the intramolecular reductive aldol reaction of alpha,beta-unsaturated esters with ketones, affording five- and six-membered beta-hydroxylactones in high stereoselectivities. Utilization of chiral nonracemic bisphosphines render the cyclizations enantioselective.
Lam
Hon Wai
HW
School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, United Kingdom. h.lam@ed.ac.uk
Joensuu
Pekka M
PM
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006900:Hydroxylation; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
D007783:Lactones; D008024:Ligands; D010720:Phosphines; D003300:Copper; C044646:phosphine