title: An iodine catalyzed metal free domino process for the stereoselective synthesis of oxygen bridged bicyclic ethers.
abstract: A domino reaction has been developed for the synthesis of oxygen bridged bicyclic ethers through the coupling of 4-(2-hydroxyethyl)cyclohex-3-enols with aldehydes in the presence of 10 mol% of molecular iodine in dichloromethane at 25 °C. This method is highly diastereoselective affording the corresponding bicyclic ethers, i.e. octahydro-4a,7-epoxyisochromenes in good yields with high selectivity. It is the first report on the synthesis of oxygen bridged bicyclic ethers using a domino Prins strategy.
authors.affiliation: Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Tarnaka, 500 007, Hyderabad, India. basireddy@iict.res.in.
authors.forename: B V Subba
authors.initials: BV
authors.lastname: Reddy
authors.forename: B
authors.initials: B
authors.lastname: Someswarao
authors.forename: N
authors.initials: N
authors.lastname: Prudhviraju
authors.forename: B Jagan Mohan
authors.initials: BJ
authors.lastname: Reddy
authors.forename: B
authors.initials: B
authors.lastname: Sridhar
authors.forename: S Kiran
authors.initials: SK
authors.lastname: Kumar
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D004987:Ethers; D007455:Iodine; D010100:Oxygen