Issue 21, 2010
From the journal:

Chemical Communications

Organocatalytic asymmetric aza-Nazarov cyclization of an azirine†

Naoyuki Shimada,a   Bradley O. Ashburn,a   Ashok K. Basak,a   William F. Bow,a   David A. Vicica  and  Marcus A. Tius*ab  

* Corresponding authors

a Department of Chemistry, University of Hawaii, 2545 The Mall, Honolulu, USA
E-mail: tius@hawaii.edu
Fax: +1 808-956-5908
Tel: +1 808-956-2779

b The Cancer Research Center of Hawaii, 1236 Lauhala Street, Honolulu, USA

Abstract

An unusual organocatalytic asymmetric cyclization of a ketoazirine that is accompanied by a kinetic resolution leads to 4-hydroxy-3-oxo-1,2,3,6-tetrahydropyridine-2-carboxylates in >99/1 er.

Graphical abstract: Organocatalytic asymmetric aza-Nazarov cyclization of an azirine

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DOI
https://doi.org/10.1039/B927564A
Article type
Communication
Submitted
05 Jan 2010
Accepted
14 Apr 2010
First published
28 Apr 2010

Chem. Commun., 2010,46, 3774-3775

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Organocatalytic asymmetric aza-Nazarov cyclization of an azirine

N. Shimada, B. O. Ashburn, A. K. Basak, W. F. Bow, D. A. Vicic and M. A. Tius, Chem. Commun., 2010, 46, 3774 DOI: 10.1039/B927564A

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