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

被引：0

作者：

Falb, E ^{[1
]}

Nudelman, A ^{[1
]}

Gottlieb, HE ^{[1
]}

Hassner, A ^{[1
]}

机构：

[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 2000卷 / 04期

关键词：

INOC; pyrrolidines; piperidines; stereoselective synthesis;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

引用

页码：645 / 655

页数：11

共 38 条

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