Issue 10, 2011
From the journal:

Chemical Science

Phosphine-catalyzed one-pot isomerization of 3-alkynoates and [2 + 3]-cycloaddition with imines: formal synthesis of Securinegaalkaloid (±)-allosecurinine†

Magesh Sampath,a   Pei-Ying Beatrix Leea  and  Teck-Peng Loh*a  

* Corresponding authors

a Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore
E-mail: teckpeng@ntu.edu.sg
Fax: +65 6515 8229
Tel: +65 6513 8475

Abstract

Trimethylphosphine-induced isomerization and cycloaddition of 3-alkynoates with imines for the synthesis of 2,5-syn di-substituted pyrrolines were described. In addition, the utility of this protocol was demonstrated in the efficient formal synthesis of the Securinegaalkaloid ‘allosecurinine’.

Graphical abstract: Phosphine-catalyzed one-pot isomerization of 3-alkynoates and [2 + 3]-cycloaddition with imines: formal synthesis of Securinegaalkaloid (±)-allosecurinine

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Article information

DOI
https://doi.org/10.1039/C1SC00311A
Article type
Edge Article
Submitted
23 May 2011
Accepted
20 Jun 2011
First published
07 Jul 2011

Chem. Sci., 2011,2, 1988-1991

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Phosphine-catalyzed one-pot isomerization of 3-alkynoates and [2 + 3]-cycloaddition with imines: formal synthesis of Securinegaalkaloid (±)-allosecurinine

M. Sampath, P. B. Lee and T. Loh, Chem. Sci., 2011, 2, 1988 DOI: 10.1039/C1SC00311A

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