title: Organocatalytic, Enantioselective Synthesis of 1- and 3-Substituted Isochromans via Intramolecular Oxa-Michael Reaction of Alkoxyboronate: Synthesis of (+)-Sonepiprazole.
abstract: The enantioselective oxa-Michael reaction of alkoxyboronate strategy was demonstrated to provide a new and practical route to enantioriched 1- and 3-substituted isochromans using a chiral bifunctional organocatalyst. Furthermore, this methodology was extended to the enantioselective synthesis of (+)-sonepiprazole, a dopamine receptor antagonist.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhauri, Bhopal-462066, India.
authors.forename: Barnala
authors.initials: B
authors.lastname: Raveendra
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhauri, Bhopal-462066, India.
authors.forename: Sanjay
authors.initials: S
authors.lastname: Maity
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhauri, Bhopal-462066, India.
authors.forename: Braja Gopal
authors.initials: BG
authors.lastname: Das
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhauri, Bhopal-462066, India.
authors.forename: Prasanta
authors.initials: P
authors.lastname: Ghorai
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry*; D000096926:Benzenesulfonamides
chemical_list: D001897:Boronic Acids; D002839:Chromans; D010879:Piperazines; D013449:Sulfonamides; C100448:sonepiprazole; D000096926:Benzenesulfonamides