Issue 15, 2008
From the journal:

Organic & Biomolecular Chemistry

Synthesis of azoxabicyclo[3.3.1]nonanones based on diastereoselective reactions of 1,1-bis(trimethylsilyloxy)ketene acetals with isoquinolines and quinolines†

Andreas Schmidt,a   Dirk Michalik,*b   Sven Rotzoll,ab   Ehsan Ullah,ab   Christine Fischer,b   Helmut Reinke,a   Helmar Görlsc  and  Peter Langer*ab  

* Corresponding authors

a Institut für Chemie, Universität Rostock, Albert-Einstein-Str., 3a, Rostock, Germany
E-mail: peter.langer@uni-rostock.de
Fax: +49 381 49864112
Tel: +49 381 4986410

b Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str., 29a, Rostock, Germany

c Institut für Anorganische und Analytische Chemie, Universität Jena, August-Bebel-Str. 2, Jena, Germany

Abstract

Densely functionalized azoxabicyclo[3.3.1]nonanones were prepared by regio- and diastereoselective condensation of 1,1-bis(silyloxy)ketene acetals with isoquinolinium and quinolinium salts and subsequent regioselective and stereospecific iodolactonization.

Graphical abstract: Synthesis of azoxabicyclo[3.3.1]nonanones based on diastereoselective reactions of 1,1-bis(trimethylsilyloxy)ketene acetals with isoquinolines and quinolines

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Article information

DOI
https://doi.org/10.1039/B804139C
Article type
Paper
Submitted
10 Mar 2008
Accepted
09 May 2008
First published
12 Jun 2008

Org. Biomol. Chem., 2008,6, 2804-2814

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Synthesis of azoxabicyclo[3.3.1]nonanones based on diastereoselective reactions of 1,1-bis(trimethylsilyloxy)ketene acetals with isoquinolines and quinolines

A. Schmidt, D. Michalik, S. Rotzoll, E. Ullah, C. Fischer, H. Reinke, H. Görls and P. Langer, Org. Biomol. Chem., 2008, 6, 2804 DOI: 10.1039/B804139C

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