From Amino Acids to Fused Chiral Pyrrolidines and Piperidines via the INOC Route

Abstract

Intramolecular nitrile oxide olefin cycloaddition (INOC) reactions of oximes 1–3 and of 24–27 derived from L-amino acids have been found to proceed stereoselectively, yielding tricyclic fused pyrrolidines and piperidines. Further manipulation led to chiral hydroxymethyl-substituted fused piperidines 33–35 and to 3-amino-4-(1-hydroxypropyl)-2-mercaptomethyl-N-methylpiperidine (36). The structures and stereochemistries of the fused systems, as well as those of the piperidines, have been established by NMR.