Molecular Iodine-Catalyzed, One-Pot, Diastereoselective Synthesis of 4-Amido Tetrahydropyrans

Author: Sabitha Gowravaram   Bhikshapathi M.   Nayak Sambit   Yadav J. S.  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.41, Iss.1, 2011-01, pp. : 8-15

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Abstract

A simple and efficient one-pot synthesis of symmetrical 4-amido tetrahydropyrans via the Sakurai-Prins-Ritter reaction sequence using molecular iodine as catalyst from an aldehyde and allyltrimethylsilane in acetonitrile is described. This new method has the advantage of good to excellent yields (60-98%) and short reaction times (20-150 min) at ambient temperature with high diastereoselectivity.