An improved synthesis of pyrroles from N??p??toluenesulfonylglycine esters and α, β??unsaturated aldehydes and ketones

TD Lash, MC Hoehner

Index: Lash, Timothy D.; Hoehner, Michael C. Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 7 p. 1671 - 1676

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Citation Number: 27

Abstract

Abstract Np-Toluenesulfonylglycine esters 2 condensed with α, β-unsaturated carbonyl compounds 1 in the presence of the non-nucleophilic base DBU to give hydroxypyrrolidines 3. Dehydration with phosphorus oxychloride-pyridine, followed by DBU mediated elimination of p-toluenesulfinic acid, gave a series of synthetically useful pyrrole-2- carboxylates 5.