Issue 12, 2011
From the journal:

Organic & Biomolecular Chemistry

Alkenylphosphonates: unexpected products from reactions of methyl 2-[(diethoxyphosphoryl)methyl]benzoate under Horner–Wadsworth–Emmons conditions†

Lynton J. Baird,a   Cédric Colomban,a   Claire Turner,a   Paul H. Teesdale-Spittleb  and  Joanne E. Harvey*a  

* Corresponding authors

a School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington 6140, New Zealand
E-mail: joanne.harvey@vuw.ac.nz
Fax: +64-4-4635237
Tel: +64-4-4635956

b School of Biological Sciences, Victoria University of Wellington, PO Box 600, Wellington 6140, New Zealand

Abstract

Methyl 2-[(diethoxyphosphoryl)methyl]benzoate reacts with several aldehydes to produce an alkenylphosphonate as the major product, together with varying amounts of the expected Horner–Wadsworth–Emmons product, a 1,2-disubstituted E-alkene. Use of a bulky aldehyde or the tert-butyl ester favours the normal HWE product.

Graphical abstract: Alkenylphosphonates: unexpected products from reactions of methyl 2-[(diethoxyphosphoryl)methyl]benzoate under Horner–Wadsworth–Emmons conditions

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Article information

DOI
https://doi.org/10.1039/C1OB05506B
Article type
Communication
Submitted
31 Mar 2011
Accepted
27 Apr 2011
First published
16 May 2011

Org. Biomol. Chem., 2011,9, 4432-4435

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Alkenylphosphonates: unexpected products from reactions of methyl 2-[(diethoxyphosphoryl)methyl]benzoate under Horner–Wadsworth–Emmons conditions

L. J. Baird, C. Colomban, C. Turner, P. H. Teesdale-Spittle and J. E. Harvey, Org. Biomol. Chem., 2011, 9, 4432 DOI: 10.1039/C1OB05506B

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