Asymmetric organocatalytic synthesis of quaternary α-hydroxy phosphonates: en route to α-aryl phosphaisoserines

Inmaculada Serrano; David Monge; Eleuterio Álvarez; Rosario Fernández; José M. Lassaletta

doi:10.1039/C4CC10390D

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Asymmetric organocatalytic synthesis of quaternary α-hydroxy phosphonates: en route to α-aryl phosphaisoserines†

Inmaculada Serrano,^a David Monge,*^a Eleuterio Álvarez,^b Rosario Fernández*^a and José M. Lassaletta*^b

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* Corresponding authors

^a Departamento de Química Orgánica, Universidad de Sevilla, C/ Prof. García González, 1, 41012 Sevilla, Spain
E-mail: dmonge@us.es, ffernan@us.es
Fax: +34 954624960
Tel: +34 954551518

^b Instituto de Investigaciones Químicas,, CSIC-US, Américo Vespucio 49, E-41092 Sevilla, Spain
E-mail: jmlassa@iiq.csic.es
Fax: +34 954460565
Tel: +34 954489563

Abstract

The dual activation of acyl phosphonates and formaldehyde tert-butyl hydrazone by a BINAM-derived bis-urea catalyst is the key to achieve high reactivities and enantioselectivities in the synthesis of densely functionalized quaternary α-hydroxy phosphonates. Subsequent high-yielding transformations in a ‘one-pot’ fashion provide direct access to valuable azoxy compounds and quaternary α-aryl-phosphaisoserines.

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DOI: https://doi.org/10.1039/C4CC10390D
Article type: Communication
Submitted: 29 Dec 2014
Accepted: 28 Jan 2015
First published: 02 Feb 2015

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Chem. Commun., 2015,51, 4077-4080

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Asymmetric organocatalytic synthesis of quaternary α-hydroxy phosphonates: en route to α-aryl phosphaisoserines

I. Serrano, D. Monge, E. Álvarez, R. Fernández and J. M. Lassaletta, Chem. Commun., 2015, 51, 4077 DOI: 10.1039/C4CC10390D

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Chemical Communications

Asymmetric organocatalytic synthesis of quaternary α-hydroxy phosphonates: en route to α-aryl phosphaisoserines†

Abstract

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Asymmetric organocatalytic synthesis of quaternary α-hydroxy phosphonates: en route to α-aryl phosphaisoserines

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