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Short Paper | Regular issue | Vol 98, No. 12, 2019, pp.1725-1735
Published online, 17th December, 2019
DOI: 10.3987/COM-19-14180
Chemoselectivity-Tunable [5 + 2] Cycloadditions of Allenamides and Oxidopyryliums

Min Yang, Liangliang Kang, and Shuzhong He*

*School of Pharmaceutical Sciences, Guizhou University, 440 Chongyi Building,Guizhou University, Huaxi District, China


[5 + 2] Cycloadditions between allenamides and oxidopyryliums are described. A series of substituted cycloheptanones were synthesized by this method with moderate to good yields. Interestingly, the chemoselectivity of this reaction could be tuned by changing the electron-withdrawing groups on the allenamide nitrogen atom. When oxazolidinone chiral auxiliaries were introduced in the allenamide substrate, [5 + 2] cycloadducts could be obtained with high diastereoselectivities. This reaction provides a useful synthetic protocol for the construction of highly substituted seven-membered rings.