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Issue 96, 2015
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Catalytic asymmetric endo-selective [3+2] cycloaddition reactions of Schiff bases of α-aminophosphonates with olefins using chiral metal amides

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Abstract

Catalytic asymmetric endo-selective [3+2] cycloaddition reactions of Schiff bases of α-aminophosphonates with olefins are described. While the efficient asymmetric synthesis of several phosphonate analogues of proline derivatives is important in bioorganic chemistry, a direct catalytic method to prepare optically active endo [3+2] cycloadducts of α-aminophosphonates with olefins has never been developed. We found for the first time that catalyst systems prepared from Group 11 metal amides with the (R)-FeSulphos ligand were effective for the asymmetric endo-selective [3+2] cycloaddition to afford the desired proline phosphonate analogues in high yields with high endo- and high enantioselectivities.

Graphical abstract: Catalytic asymmetric endo-selective [3+2] cycloaddition reactions of Schiff bases of α-aminophosphonates with olefins using chiral metal amides

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Supplementary files

Article information


Submitted
22 Aug 2015
Accepted
09 Sep 2015
First published
09 Sep 2015

Chem. Commun., 2015,51, 17064-17067
Article type
Communication
Author version available

Catalytic asymmetric endo-selective [3+2] cycloaddition reactions of Schiff bases of α-aminophosphonates with olefins using chiral metal amides

Y. Yamashita, L. C. Nam, M. J. Dutton, S. Yoshimoto and S. Kobayashi, Chem. Commun., 2015, 51, 17064
DOI: 10.1039/C5CC07066J

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