Stereoselective Synthesis of 1,3-Dienes from Propargylic Alcohols by LiAlH4/AlCl3 |
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| Authors: | Dong-Mei Cui Kai Zhu Li Chen Lang-Jun Qi Cheng-Zhu Zhang Chen Zhang |
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| Institution: | 1. College of Pharmaceutical Science, Zhejiang University of Technology , Hangzhou , China cuidongmei@zjut.edu.cn;3. College of Pharmaceutical Science, Zhejiang University of Technology , Hangzhou , China;4. College of Pharmaceutical Sciences, Zhejiang University , Hangzhou , China |
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| Abstract: | Herein we report that LiAlH4/AlCl3 is a very efficient reagent for the reductive dehydration of aryl propargylic alcohols in tetrahydrofuran solvent at reflux to give 1,3-dienes with good yields and high E selection. The reaction conditions are mild and easy to operate, and a variety of aryl functional groups, such as bromo, fluoro, butyl, and methoxyl groups, are tolerated. With our protocol, useful (E,E)-1,3-dienes can be synthesized. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file. |
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| Keywords: | Dehydration 1 3-diene propargylic alcohol reduction stereoselection |
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