Tetrahedron Letters

Water-compatible one-pot organocatalytic asymmetric synthesis of cyclic nitrones. Application in intramolecular 1, 3-dipolar cycloadditions

D Sádaba, I Delso, T Tejero, P Merino

Index: Sadaba, David; Delso, Ignacio; Tejero, Tomas; Merino, Pedro Tetrahedron Letters, 2011 , vol. 52, # 45 p. 5976 - 5979

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Citation Number: 6

Abstract

Optically active five-membered cyclic nitrones are readily obtained in a one-pot procedure via the organocatalytic Michael addition of aldehydes to nitroolefins and in situ reductive cyclization. Application of the methodology to the synthesis of tricyclic compounds through intramolecular 1, 3-dipolar cycloaddition reactions (DFT calculations have also been performed) is also demonstrated. All the reactions were carried out in water as a solvent ...