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

1991; Wiley; Volume: 28; Issue: 7 Linguagem: Inglês

10.1002/jhet.5570280705

1943-5193

Timothy D. Lash, M. C. HOEHNER,

Organic Chemistry Cycloaddition Reactions

Abstract N‐p ‐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 .