Issue 4, 2003
From the journal:

New Journal of Chemistry

Synthesis of the new 2-azatricyclo[3.3.0.03,6]octane skeleton as a constrained proline analogue

Thomas Rammelooa  and  Christian V. Stevens*a  

* Corresponding authors

a Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure links 653, Gent, Belgium
E-mail: Chris.Stevens@rug.ac.be
Fax: +32-9-264 62 43
Tel: +32-9-264 59 57

Abstract

The synthesis of the tricyclic amino ester 12 is described. This constrained proline analogue contains the formerly unknown 2-azatricyclo[3.3.0.03,6]octane skeleton. A short 5 step sequence was developed allowing the production of 12 on a multi-gram scale. The key step consists of a stereoselective synthesis of a hydantoin that, after conversion to the amino ester, can be brominated and ring closed to the 2-azatricyclo[3.3.0.03,6]octane skeleton.

Graphical abstract: Synthesis of the new 2-azatricyclo[3.3.0.03,6]octane skeleton as a constrained proline analogue

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Article information

DOI
https://doi.org/10.1039/B300331K
Article type
Letter
Submitted
09 Jan 2003
Accepted
24 Feb 2003
First published
04 Mar 2003

New J. Chem., 2003,27, 668-671

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Synthesis of the new 2-azatricyclo[3.3.0.03,6]octane skeleton as a constrained proline analogue

T. Rammeloo and C. V. Stevens, New J. Chem., 2003, 27, 668 DOI: 10.1039/B300331K

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