title: Stereoselective synthesis of indolines via organocatalytic thioester enolate addition reactions.
abstract: A straightforward stereoselective synthesis route to indolin-3-yl acetates has been developed using organocatalytic addition reactions of monothiomalonates to ortho-bromo nitrostyrenes as the key step. The addition products of this highly stereoselective one-pot addition-deprotection-decarboxylation sequence were easily further converted to the target indolin-3-yl acetates, via an intramolecular Buchwald-Hartwig coupling reaction. The route provided indolin-3-yl acetates bearing tertiary and exocyclic quarternary stereogenic centers in excellent stereoselectivities and overall yields of 34-83%.
authors.affiliation: ETH Zürich , Laboratorium für Organische Chemie, Vladimir-Prelog-Weg 3, CH-8093 Zürich, Switzerland.
authors.forename: Andrej
authors.initials: A
authors.lastname: Kolarovic
authors.forename: Alexander
authors.initials: A
authors.lastname: Käslin
authors.forename: Helma
authors.initials: H
authors.lastname: Wennemers
mesh_terms: D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D002264:Carboxylic Acids; D007211:Indoles; C057812:indoline