title: Palladium-Catalyzed Internal Nucleophile-Assisted Hydration-Olefin Insertion Cascade: Diastereoselective Synthesis of 2,3-Dihydro-1H-inden-1-ones.
abstract: A novel palladium-catalyzed hydration-olefin insertion cascade assisted by internal nucleophiles was developed for the synthesis of biologically significant 2,3-dihydro-1H-inden-1-ones under mild conditions. A detailed mechanistic study revealed that the assistance of the internal nucleophiles is crucial to trigger the cascade reaction via nucleopalladation of the alkyne moiety. The overall reaction is equivalent to regioselective hydration of alkynes followed by intramolecular Michael addition. This highly efficient and 100% atom-economical domino sequence afforded cis-2,3-disubstituted 2,3-dihydro-1H-inden-1-ones in excellent yields (up to 99%) with complete diastereoselectivity.
authors.affiliation: Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University , Thanjavur 613 401, Tamil Nadu, India.
authors.forename: Perumal
authors.initials: P
authors.lastname: Vinoth
authors.affiliation: Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University , Thanjavur 613 401, Tamil Nadu, India.
authors.forename: Subbiah
authors.initials: S
authors.lastname: Nagarajan
authors.affiliation: Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University , Thanjavur 613 401, Tamil Nadu, India.
authors.forename: C Uma
authors.initials: CU
authors.lastname: Maheswari
authors.affiliation: Chemical Engineering and Process Development Division, National Chemical Laboratory , Pashan Road, Pune 411 008, India.
authors.forename: Arumugam
authors.initials: A
authors.lastname: Sudalai
authors.affiliation: Department of Pharmaceutical Chemistry, University of Vienna , Althanstrasse 14, A-1090 Vienna, Austria.
authors.forename: Vittorio
authors.initials: V
authors.lastname: Pace
authors.affiliation: Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University , Thanjavur 613 401, Tamil Nadu, India.
authors.forename: Vellaisamy
authors.initials: V
authors.lastname: Sridharan