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Synlett 2010(20): 3057-3060  
DOI: 10.1055/s-0030-1259068
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

First Application of Air-Stable and Reusable Phosphine-Containing Calix[4]arene in Catalytic Aza-Morita-Baylis-Hillman Reaction

Weihui Zhong*, Yemin Zheng, Jiadi Zhou, Yanyan Shen
Key Laboratory of Pharmaceutical Engineering of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Fax: +86(571)88320752; e-Mail: pharmlab@zjut.edu.cn;
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Publication History

Received 2 September 2010
Publication Date:
24 November 2010 (online)

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Abstract

For the first time, the aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone was catalyzed by 5,11,17,23-tetrabutyl-25-(diphenylphosphinomethoxy)-26,27,28-­trihydroxycalix[4]arene (LB1), an air-stable, easily isolated and reusable catalyst. Great acceleration of the reaction was observed and the aza-Morita-Baylis-Hillman adducts were produced in excellent yields within short reaction time.

Key words

calix[4]arene - organocatalyst - phosphine - reusable - aza-Morita-Baylis-Hillman

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