Tetrahedron letters

On the Ritter reaction of cyclic hydroxyamines: Synthesis of conformationally-restricted reduced amide dipeptide isosteres

GM Taylor, SJ Baker, A Gedney, DJ Pearson…

Index: Taylor, G. Mark; Baker, Stewart J.; Gedney, Andrea; Pearson, David J.; Sibley, Graham E. M. Tetrahedron Letters, 1996 , vol. 37, # 8 p. 1297 - 1300

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Citation Number: 11

Abstract

The Ritter reactions of 3-alkyl-3-hydroxyazetidine or-piperidine derivatives give low yields of the desired products, whereas the 3-alkyl-3-hydroxy-pyrrolidine and 4-alkyl-4-hydroxy- piperidine derivatives react smoothly to give the corresponding acetamides. An alternative route to 3-acylamino-3-alkylpiperidines, which were designed as conformationally-restricted reduced amide dipeptide isosteres, was devised from nipecotic acid via a Hofmann ...