Stereoselective Synthesis of (2Z)-2,4-Dienamides via NBS-Mediated Allyloxyl Addition-Claisen Rearrangement-Dehydrobromination Cascade Reaction of Ynsulfonamides

Runbo Ding, Yun Li*, Cheng Tao, Bin Cheng and Hongbin Zhai*

*The State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, China, Email: zhaihlzu.edu.cn, liyunlzu.edu.cn

R. Ding, Y. Li, C. Tao, B. Cheng, H. Zhai, Org. Lett., 2015, 17, 3994-3997.

DOI: 10.1021/acs.orglett.5b01859

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Abstract

In an NBS-promoted allyloxyl addition-Claisen rearrangement-dehydrobromination cascade reaction, more than 20 substituted alkynylsulfonamides were reacted with allyl alcohols to generate (2Z)-2,4-dienamides in good yields. Theoretical calculations suggested that a [3,3] sigmatropic rearrangement be the rate-limiting step.

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Key Words

dienes, amides, NBS

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ID: J54-Y2015