title: Construction of perhydro indol-2-ones by a methoxide catalyzed deacetylation-Michael-aldol cascade.
abstract: An efficient, stereoselective Michael-aldol cascade for the one-pot construction of the perhydro indol-2-one bicyclic ring system using an acetate protected doubly-activated pyrrole-2-one pro-nucleophile and alpha,beta-unsaturated carbonyl compounds has been developed. Initiated by a methoxide deacetylation in methanol at room temperature, the cascade is easy to perform, stereoselective, efficient and broad in scope to this synthetically relevant structure.
authors.affiliation: School of Chemistry, The University of Manchester, Oxford Road, Manchester, UKM13 9PL.
authors.forename: John W
authors.initials: JW
authors.lastname: Ward
authors.forename: Karen
authors.initials: K
authors.lastname: Dodd
authors.forename: Caroline L
authors.initials: CL
authors.lastname: Rigby
authors.forename: Chris
authors.initials: C
authors.lastname: De Savi
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
mesh_terms: D000107:Acetylation; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D007536:Isomerism; D000432:Methanol / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D007211:Indoles; C116609:3-hydroxybutanal; D000432:Methanol