Stereoselective synthesis of spirooxindole amides through nitrile hydrozirconation.
Spirooxindole amides can be prepared by the intramolecular addition of functionalized indoles into acylimines that are accessed from nitriles by hydrozirconation and acylation. The stereochemical outcome at the quaternary center was controlled by the steric bulk of the substituent at the 2-position of the indole unit. The products are well-suited for diversification to prepare libraries.
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.
Chunliang
C
Lu
Qing
Q
Xiao
Paul E
PE
Floreancig
D000215:Acylation; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D007211:Indoles; D009570:Nitriles; D013141:Spiro Compounds