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Synthesis 2010(18): 3204-3210  
DOI: 10.1055/s-0030-1258172
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Phosphazene Base-Catalyzed Intramolecular Cascade Reactions of Aryl-Substituted Enynes

Jian-Sheng Tanga,b, Ye-Xiang Xiea, Zhi-Qiang Wanga, Chen-Liang Denga, Jin-Heng Li*a
a Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(731)88872101; e-Mail: jhli@hunnu.edu.cn;
b Mathematics and Science Department, Hunan First Normal University, Changsha, 410205, P. R. of China
Further Information

Publication History

Received 6 April 2010
Publication Date:
12 July 2010 (online)

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Abstract

A novel method for the synthesis of 9-aryl-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-ones has been developed by P4-t-Bu-catalyzed intramolecular cascade reactions of enynes. In the presence of a catalytic amount of phosphazene P4-t-Bu base, a variety of 3-arylallyl 3-arylpropiolates underwent the cascade cyclization reaction smoothly in moderate to excellent yields.

Key words

P4-t-Bu base - cascade cyclization reaction - 9-aryl-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one - 3-arylallyl 3-arylpropiolate

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The X-ray crystallographic data for compound 2a are summarized in Supporting Information.