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

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.

Keywords:

• Aldehydes
• allyltrimethylsilane
• diastereoselectivity
• iodine
• Sakurai–Prins–Ritter
• tetrahydropyrans

ACKNOWLEDGMENT

M.B. and S.N. thank the Council of Scientific and Industrial Research, New Delhi, for the award of fellowships.

Notes

^a All products were characterized by spectral data and confirmed by NOE studies.

^b Isolated pure products.

^a All products were characterized by spectral data and confirmed by NOE studies.

^b Isolated pure products.