CuH-catalyzed enantioselective intramolecular reductive aldol reactions generating three new contiguous asymmetric stereocenters.
Treatment of beta,beta-disubstituted-alpha,beta-unsaturated ketones bearing a ketone residue with in situ generated, catalytic CuH ligated by a nonracemic ligand leads to three newly created adjacent chiral centers. Excellent de's and ee's are obtained for several examples studied.
Lipshutz
Bruce H
BH
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA. lipshutz@chem.ucsb.edu
Amorelli
Benjamin
B
Unger
John B
JB
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000438:Alcohols; D003510:Cyclohexanes; D007659:Ketones; D003300:Copper