Synthetic and Mechanistic Studies of the Aza-Retro-Claisen Rearrangement. A Facile Route to Medium Ring Nitrogen Heterocycles
Organic Letters2010Vol. 12(7), pp. 1628–1631
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Abstract
An efficient synthesis of medium-sized heterocyclic rings was achieved using a one-pot aza-Wittig/retro-aza-Claisen sequence of vinyl cyclobutanecarboxaldehydes derived from simple allylic carbonates. The use of various Staudinger reagents in the aza-Wittig reaction allows for a variety of N-substituted products to be obtained. The rearrangement is under thermodynamic control driven by relief of the cyclobutane ring strain and resonance stabilization of the resulting vinylogous amide/sulfonamide.
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