TY - JOUR
T1 - From amino acids to fused chiral pyrrolidines and piperidines via the INOC route
AU - Falb, Eliezer
AU - Nudelman, Abraham
AU - Gottlieb, Hugo E.
AU - Hassner, Alfred
PY - 2000/2
Y1 - 2000/2
N2 - 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.
AB - 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.
KW - INOC
KW - Piperidines
KW - Pyrrolidines
KW - Stereoselective synthesis
UR - https://www.scopus.com/pages/publications/0034089041
U2 - 10.1002/(SICI)1099-0690(200002)2000:4<645::AID-EJOC645>3.0.CO;2-I
DO - 10.1002/(SICI)1099-0690(200002)2000:4<645::AID-EJOC645>3.0.CO;2-I
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AN - SCOPUS:0034089041
SN - 1434-193X
SP - 645
EP - 655
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 4
ER -