Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles.
A highly regio-, diastereo-, and enantioselective allylic alkylation reaction mediated by a chiral molybdenum catalyst has been developed as a novel entry into synthetically versatile 3-alkyl-3-aryloxindoles. Extremely bulky nucleophiles were employed to form a quaternary center and an adjacent tertiary center asymmetrically concurrently. The regio- and diastereoselectivity of the reaction is dependent upon the steric and electronic nature of the nucleophiles to an unusual degree. A reaction mechanism based on the bonding modes of molybdenum enolate complexes was discussed.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Zhang
Yong
Y
D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism
D000498:Allyl Compounds; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D008982:Molybdenum