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Intramolecular-Prins-cyclization: a novel synthesis of hexahydro-2H-furo[3,2-c]pyran derivatives
Authors:J.S. Yadav  P. Pawan Chakravarthy  Prashant Borkar  B.V. Subba Reddy  A.V.S. Sarma
Affiliation:Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Abstract:p-Toluenesulfonic acid is found to catalyze the coupling of (Z)-hex-3-ene-1,6-diol with a series of aldehydes by means of intramolecular-Prins-cyclization to provide the corresponding hexahydro-2H-furo[3,2-c]pyran derivatives in good yields with complete cis-selectivity, whereas the coupling of (E)-hex-3-ene-1,6-diol with aliphatic aldehydes gave trans-fused bicyclic furopyrans.
Keywords:Brø  nsted acids   Intramolecular-Prins-cyclization   Angularly fused furopyrans
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