Issue 48, 2011
From the journal:

Chemical Communications

On the stereoselective bicyclization of aminodienes catalyzed by chelating diamide complexes of the group 3 metals. A direct comparison of Sc(iii) and Y(iii) bis(amide)s with an application to the synthesis of alkaloid 195F†

Tao Jiang,a   Tom Livinghouse*a  and  Helena M. Lovicka  

* Corresponding authors

a Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT, USA
E-mail: Livinghouse@chemistry.montana.edu
Fax: (406) 994-5407
Tel: (406) 994-5408

Abstract

Highly diastereoselective bicyclizations of aminodienes catalyzed by chelating diamide complexes of Sc(III) and Y(III) that lead to pyrrolizidines and indolizidines are described. This bis(annulation) procedure has been utilized in a concise synthesis of the pyrrolizidine alkaloid 195F.

Graphical abstract: On the stereoselective bicyclization of aminodienes catalyzed by chelating diamide complexes of the group 3 metals. A direct comparison of Sc(iii) and Y(iii) bis(amide)s with an application to the synthesis of alkaloid 195F

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Article information

DOI
https://doi.org/10.1039/C1CC15399D
Article type
Communication
Submitted
30 Aug 2011
Accepted
09 Oct 2011
First published
02 Nov 2011

Chem. Commun., 2011,47, 12861-12863

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On the stereoselective bicyclization of aminodienes catalyzed by chelating diamide complexes of the group 3 metals. A direct comparison of Sc(III) and Y(III) bis(amide)s with an application to the synthesis of alkaloid 195F

T. Jiang, T. Livinghouse and H. M. Lovick, Chem. Commun., 2011, 47, 12861 DOI: 10.1039/C1CC15399D

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