Studies on the regioselectivity of Horner-Wadsworth-Emmons (HWE) reactions on 3,4-enuloses. Further evidence of phosphonate-phosphate rearrangements through five membered cyclic intermediates

Article abstract of DOI:10.1080/07328309908544032

The Horner-Wadsworth-Emmons (HWE) reaction was performed on methyl 3,6-di-0-benzoyl-2-deoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (1) with the potassium enolates of dimethyl [(methoxycarbonyl)methyl]phosphonate (2) or diethyl [(ethoxycarbonyl) methyl]pho

Full text of DOI:10.1080/07328309908544032

This article was downloaded by: [University of Stellenbosch]
On: 06 October 2014, At: 20:28
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954
Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Journal of Carbohydrate Chemistry
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/lcar20
Studies on the Regioselectivity of
Horner-Wadsworth-Emmons (Hwe)
Reactions on 3,4-Enuloses. Further
Evidence of Phosphonate-Phosphate
Rearrangements Through Five
Membered Cyclic Intermediates.
Oscar M. Moradei , Cecile M. du Mortier & Alicia Fernández
Cirelli
a CIHIDECAR Departamento de Química Orgánica, Facultad de
Ciencias Exactas y Naturales, Universidad de Buenos Aires,
Ciudad Universitaria , Pab. II, 1428 Buenos Aires, Argentina
b CIHIDECAR Departamento de Química Orgánica, Facultad de
Ciencias Exactas y Naturales, Universidad de Buenos Aires,
Ciudad Universitaria , Pab. II, 1428 Buenos Aires, Argentina
c CIHIDECAR Departamento de Química Orgánica, Facultad de
Ciencias Exactas y Naturales, Universidad de Buenos Aires,
Ciudad Universitaria , Pab. II, 1428 Buenos Aires, Argentina
Published online: 27 Feb 2008.
To cite this article: Oscar M. Moradei , Cecile M. du Mortier & Alicia Fernández Cirelli
(1999) Studies on the Regioselectivity of Horner-Wadsworth-Emmons (Hwe) Reactions on
3,4-Enuloses. Further Evidence of Phosphonate-Phosphate Rearrangements Through Five
Membered Cyclic Intermediates., Journal of Carbohydrate Chemistry, 18:6, 709-719, DOI:
10.1080/07328309908544032
To link to this article: http://dx.doi.org/10.1080/07328309908544032
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information
(the “Content”) contained in the publications on our platform. However, Taylor
& Francis, our agents, and our licensors make no representations or warranties
whatsoever as to the accuracy, completeness, or suitability for any purpose of the
Content. Any opinions and views expressed in this publication are the opinions and

views of the authors, and are not the views of or endorsed by Taylor & Francis. The
accuracy of the Content should not be relied upon and should be independently
verified with primary sources of information. Taylor and Francis shall not be liable
for any losses, actions, claims, proceedings, demands, costs, expenses, damages,
and other liabilities whatsoever or howsoever caused arising directly or indirectly in
connection with, in relation to or arising out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden.
Terms & Conditions of access and use can be found at http://www.tandfonline.com/
page/terms-and-conditions