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Reaction of Allenyl Esters with Sodium Azide:  An Efficient Synthesis of E-Vinyl Azides and Polysubstituted Pyrroles

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journal contribution
posted on 16.02.2007, 00:00 by Xian Huang, Ruwei Shen, Tiexin Zhang
The nucleophilic addition of sodium azide to 1,2-allenyl esters can generate vinyl azides in excellent yields with excellent regio- and stereoselectivities. Moreover, pyrroles are synthesized using 1-allyllic 1,2-allenyl esters as substrates in t-BuOH at 65 °C. The sequential reaction for pyrroles is developed on the basis of a novel domino process involving nucleophilic addition, cycloaddition, denitrogenation, and aromatization.