- An iodine catalyzed metal free domino process for the stereoselective synthesis of oxygen bridged bicyclic ethers.
An iodine catalyzed metal free domino process for the stereoselective synthesis of oxygen bridged bicyclic ethers.
Organic & biomolecular chemistry (2015-05-23)
B V Subba Reddy, B Someswarao, N Prudhviraju, B Jagan Mohan Reddy, B Sridhar, S Kiran Kumar
PMID25994362
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.
MATERIALS