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From Amino Acids to Fused Chiral Pyrrolidines and Piperidines via the INOC Route (2000)

Falb, Eliezer ; Nudelman, Abraham ; Gottlieb, Hugo E. ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 645-655

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Details

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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