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. 2020 Jul 13;59(29):11769-11773.
doi: 10.1002/anie.201916449. Epub 2020 May 18.

Taming the Reactivity of Phosphiranium Salts: Site-Selective C-Centered Ring Opening for Direct Synthesis of Phosphinoethylamines

Julien Gasnot  1 , Clément Botella  1 , Sébastien Comesse  1 , Sami Lakhdar  2 , Carole Alayrac  2 , Annie-Claude Gaumont  2 , Vincent Dalla  1 , Catherine Taillier  1
Affiliations

Taming the Reactivity of Phosphiranium Salts: Site-Selective C-Centered Ring Opening for Direct Synthesis of Phosphinoethylamines

Julien Gasnot et al. Angew Chem Int Ed Engl. .

Abstract

Advances in the field of phosphorus chemistry are documented, by revealing the synthetic utility of previously underutilized quaternary phosphiranium salts (QPrS) as three-chain-atom electrophilic building blocks. Notably, control of their challenging C-centered electrophilicity is disclosed with an expedient synthesis of tertiary β-anilino phosphines as a proof-of-concept.

Keywords: nucleophilic ring opening; phosphinoethyl amines; phosphiranium ions; selectivity; steric protection.

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References

    1. None
    1. Aziridines and epoxides in organic synthesis (Ed.: A. K. Yudin), Wiley-VCH, Weinheim, 2006;
    1. W. H. Pearson, B. W. Lian, S. C. Bergmeier in Comprehensive Heterocyclic Chemistry II, Vol. 1A (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, chap. 1, p. 1;
    1. I. Erden in Comprehensive Heterocyclic Chemistry II, Vol. 1A (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon Press, Oxford, 1996, chap. 3, p. 97.
    1. S. Stanković, M. D'hooghe, S. Catak, H. Eum, M. Waroquier, V. Van Speybroeck, N. De Kimpe, H.-J. Ha, Chem. Soc. Rev. 2012, 41, 643.

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