Tetrahedron letters

A facile synthesis of N-benzyl-4-acetylproline via a tandem cationic aza-Cope rearrangement-Mannich reaction

A Cooke, J Bennett, E McDaid

Index: Cooke, Andrew; Bennett, Jonathan; McDaid, Emma Tetrahedron Letters, 2002 , vol. 43, # 5 p. 903 - 905

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Citation Number: 19

Abstract

N-Benzyl-4-acetylproline can be prepared from N-(2-hydroxy-2-methyl) but-3-enyl-N- benzylamine and glyoxylic acid via a tandem cationic aza-Cope rearrangement-Mannich reaction. This reaction represents the first example of such a mechanism being utilised for the synthesis of functionalised proline derivatives. In addition the reaction requires only mild conditions and a good yield of amino acid product is obtained without any need for ...