187. Diastereo- and enantioselective syntheses of (–)-coniine, (–)-solenopsin A, (–)-solenopsis fugaz venom and (–)-xenovenine via deoxygenative decarboxylation of 2-carbonylsultam-substituted n-hydroxy-piperidines and -pyrrolidines
     Oppolzer, W.; Bochet, C. G.; Merifield, E.
     Tetrahedron Lett. 1994, 35, 7015-7018

Heating cyclic 2-carbonylsultam-substituted N-hydroxylamines 4 with NaH yields sultam auxiliary 8 and imines 10, which are trapped in situ either by i-Bu₂AlH or organocerium reagents to give enantiomerically pure 2-mono- or trans-2,6(2,5)-disubstituted piperidines (pyrrolidines) 11 or 12.

DOI : 10.1016/0040-4039(94)88213-4 

archive ouverte unige:151913