Issue 10, 2003
From the journal:

Chemical Communications

Stereoselective aza-Diels–Alder reactions with 2H-azirines as dienophiles furnishing highly functionalized tetrahydropyridines

Åsa Sjöholm Timén,a   Andreas Fischerb  and  Peter Somfai*a  

* Corresponding authors

a Organic Chemistry, Department of Chemistry, The Royal Institute of Technology, S-100 44 Stockholm, Sweden
E-mail: Somfai@kth.se
Fax: +46 8 791 23 33
Tel: +46 8 790 6960

b Inorganic Chemistry, Department of Chemistry, The Royal Institute of Technology, S-100 44 Stockholm, Sweden

Abstract

Highly diastereoselective Lewis acid mediated aza-Diels–Alder reactions of chiral auxiliary derivatized 2H-azirines have been accomplished for the first time, yielding bi and tri-cyclic heterocyclic compounds, comprising aziridine and tetrahydropyridine substructures, in up to 97% de; with the absolute stereochemistry of the major product confirmed by X-ray crystallography.

Graphical abstract: Stereoselective aza-Diels–Alder reactions with 2H-azirines as dienophiles furnishing highly functionalized tetrahydropyridines

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Article information

DOI
https://doi.org/10.1039/B300849E
Article type
Communication
Submitted
23 Jan 2003
Accepted
19 Mar 2003
First published
16 Apr 2003

Chem. Commun., 2003, 1150-1151

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Stereoselective aza-Diels–Alder reactions with 2H-azirines as dienophiles furnishing highly functionalized tetrahydropyridines

Å. S. Timén, A. Fischer and P. Somfai, Chem. Commun., 2003, 1150 DOI: 10.1039/B300849E

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