Issue 18, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Stereoselective and regioselective synthesis of azepane and azepine derivatives viapiperidinering expansion

Hyun-soon Chong,a   Bishwajit Ganguly,b   Grant A. Broker,c   Robin D. Rogersc  and  Martin W. Brechbiel*a  

* Corresponding authors

a Chemistry Section, Radiation Oncology Branch, National Cancer Institute, Building 10, Rm B3B69, NIH, Bethesda, MD 20892, USA
E-mail: martinwb@mail.nih.gov
Fax: +1 301 402-1923

b Central Salt and Marine Chemicals Research Institute, G. B. Marg, Bhavagar-364002, Gujarat, India

c Department of Chemistry, The University of Alabama, Tuscaloosa, AL, 35487, USA

Abstract

Diastereomerically pure azepane derivatives 5, 13 were prepared by piperidine ring expansion with exclusive stereoselectivity and regioselectivity and in excellent yield. The structure and stereochemistry of 5 were confirmed via X-ray crystallographic analysis. The ring expansion strategy was applied to the construction of an azepine backbone 22 of a potential biologically active compound. The regiochemistry and stereochemistry of the piperidine ring expansion process were investigated by semiempirical molecular orbital calculations.

Graphical abstract: Stereoselective and regioselective synthesis of azepane and azepine derivatives via piperidine ring expansion

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Article information

DOI
https://doi.org/10.1039/B204677F
Article type
Paper
Submitted
14 May 2002
Accepted
12 Jul 2002
First published
15 Aug 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 2080-2086

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Stereoselective and regioselective synthesis of azepane and azepine derivatives via piperidine ring expansion

H. Chong, B. Ganguly, G. A. Broker, R. D. Rogers and M. W. Brechbiel, J. Chem. Soc., Perkin Trans. 1, 2002, 2080 DOI: 10.1039/B204677F

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