ISSN:
1434-193X
Keywords:
INOC
;
Pyrrolidines
;
Piperidines
;
Stereoselective synthesis
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
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