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Synthesis 2012(7): 1119-1125  
DOI: 10.1055/s-0031-1289717
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Base-Mediated Tandem Reaction of α-Aryloxyacetophenones with Phosphonates: Selective Synthesis of Enol Phosphates

Ren-Jie Songa, Yan-Yun Liua,b, Ji-Cheng Wua,b, Ye-Xiang Xie*a, Guo-Bo Denga, Xu-Heng Yanga,b, Yu Liua, Jin-Heng Li*a
a State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China
Fax: +86(731)88872531; e-Mail: jhli@hnu.edu.cn; e-Mail: xieyexiang520@126.com;
b Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
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Publication History

Received 21 December 2011
Publication Date:
17 February 2012 (online)

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Abstract

A new, simple method for the synthesis of enol phosphates by base-mediated tandem reaction of α-aryloxyacetophenones with phosphonates is described. In the presence of Cs2CO3, a variety of α-aryloxyacetophenones smoothly underwent the sequential O-P bond-forming/C-O bond cleavage/isomerization tandem reaction with phosphonates at room temperature, providing the corresponding enol phosphates in moderate to excellent yields.

Key words

base - tandem reaction - α-aryloxyacetophenone - phosphonate - enol phosphate

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