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.
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA. lipshutz@chem.ucsb.edu
Bruce H
BH
Lipshutz
Benjamin
B
Amorelli
John B
JB
Unger
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