Amino acid derived intramolecular 1,3-dipolar cycloadditions that form bridged medium ring systems with diastereoselective control

Intramolecular nitrone cycloadditions using amino acid precursors, generate aminohydroxyazepine and amino hydroxypiperidine templates. The cycloaddition reactions yield either a [4.3.0] fused system or in most cases a [4.2.1] bridged system. The [4.2.1] bridged system allows for the stereospecific p...

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Bibliographic Details
Published in:Tetrahedron 2002-04, Vol.58 (16), p.3159-3170
Main Authors: Liu, Yanbin, Maden, Amy, Murray, William V
Format: Article
Language:English
Subjects:
cycloaddition
diastereoselective
isoxazolidine
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Summary:Intramolecular nitrone cycloadditions using amino acid precursors, generate aminohydroxyazepine and amino hydroxypiperidine templates. The cycloaddition reactions yield either a [4.3.0] fused system or in most cases a [4.2.1] bridged system. The [4.2.1] bridged system allows for the stereospecific preparation of 3-amino-5-hydroxyazepines while the [4.3.0] system allows for the preparation of 3-amino-5-hydroxymethyl piperidines. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00242-9