Catalytic double stereoinduction in asymmetric allylic alkylation of oxindoles.
A highly regio-, diastereo-, and enantioselective allylic alkylation reaction of 3-monosubstituted oxindoles catalyzed by molybdenum is described. The reaction is affected by the electronic and steric variations of the nucleophile. The use of appropriate N-protecting group is particularly important for achieving high regio- and diastereoselectivity. Products from this reaction, containing vicinal quaternary-tertiary stereogenic centers, are valuable synthetic intermediates and should find utility in alkaloid synthesis.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, CA 94305, USA. bmtrost@stanford.edu
Zhang
Yong
Y
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D008982:Molybdenum / Q000737:chemistry; D000078183:Oxindoles; D013237:Stereoisomerism
D000470:Alkaloids; D000498:Allyl Compounds; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D008982:Molybdenum