title: Organocatalytic, enantioselective, intramolecular oxa-Michael reaction of alkoxyboronate: a new strategy for enantioenriched 1-substituted 1,3-dihydroisobenzofurans.
abstract: An unprecedented strategy for the synthesis of enantioenriched 1-substituted 1,3-dihydroisobenzofurans via an enantioselective oxa-Michael reaction of o-alkoxyboronate containing chalcone (II) has been accomplished employing cinchona alkaloid based squaramide bifunctional organocatalyst in the presence of proton source. The corresponding alkoxyboronate intermediates have been readily prepared in situ from o-formyl chalcones using neutral borane as hydride source and a tertiary amine moiety which is a counterpart of the catalyst.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhauri, Bhopal 462066, India.
authors.forename: Barnala
authors.initials: B
authors.lastname: Raveendra
authors.forename: Braja Gopal
authors.initials: BG
authors.lastname: Das
authors.forename: Prasanta
authors.initials: P
authors.lastname: Ghorai
mesh_terms: D000588:Amines / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D047188:Chalcones / Q000737:chemistry*; D002930:Cinchona Alkaloids; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000588:Amines; D001572:Benzofurans; D001880:Boranes; D001897:Boronic Acids; D047188:Chalcones; D002930:Cinchona Alkaloids