Diastereoselective ritter reactions of chiral cyclic N-acyliminium ions: synthesis of pyrido- and pyrrolo [2,3-d] oxazoles and 4-hydroxy-5-N-acylaminopyrrolidines and 5-hydroxy-6-N-acylaminopiperidines

Authors

Ian R. Morgan, University of WollongongFollow
Arife Yazici, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow
Brian W. Skelton, University of Western Australia

RIS ID

25504

Publication Details

Morgan, I. R., Yazici, A., Pyne, S. G. & Skelton, B. W. (2008). Diastereoselective ritter reactions of chiral cyclic N-acyliminium ions: synthesis of pyrido- and pyrrolo [2,3-d] oxazoles and 4-hydroxy-5-N-acylaminopyrrolidines and 5-hydroxy-6-N-acylaminopiperidines. The Journal of Organic Chemistry, 73 (7), 2943-2946.

Abstract

Pyrido- and pyrrolo[2,3-d]oxazoles can be conveniently prepared in high yield from the Ritter reaction of nitriles and in situ generated chiral cyclic N-acyliminium ions. cis-4-Hydroxy-5-acylaminopyrrolidines and cis-5-hydroxy-6-acylaminopiperidines can be readily obtained by acid hydrolysis of these bicyclic heterocyclic compounds, respectively.