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From amino acids to fused chiral pyrrolidines and piperidines via the INOC route

DOI: 10.1002/(SICI)1099-0690(200002)2000:4<645::AID-EJOC645>3.0.CO;2-I

Source and publish data:

European Journal of Organic Chemistry p. 645 - 655 (2000)

Update date:2022-08-04

Topics:

Authors:

Falb, EliezerFalb, Eliezer

Nudelman, AbrahamNudelman, Abraham

Gottlieb, Hugo E.Gottlieb, Hugo E.

Hassner, AlfredHassner, Alfred

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Article abstract of DOI:10.1002/(SICI)1099-0690(200002)2000:4<645::AID-EJOC645>3.0.CO;2-I

Intramolecular nitrile oxide olefin cycloaddition (INOC) reactions of oximes 1-3 and of 24-27 derived from 1-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.

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Full text of DOI:10.1002/(SICI)1099-0690(200002)2000:4<645::AID-EJOC645>3.0.CO;2-I

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