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Catalytic Asymmetric Acyloin Rearrangements of α-Ketols, α-Hydroxy Aldehydes, and α-Iminols by N,N'-Dioxide-Metal Complexes

Li Dai, Xiangqiang Li, Zi Zeng, Shunxi Dong, Yuqiao Zhou*, Xiaohua Liu and Xiaoming Feng*

*Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China, Email:,

L. Dai, X. Li, Z. Zeng, S. Dong, Y. Zhou, X. Liu, X. Feng, Org. Lett., 2020, 22, 5041-5045.

DOI: 10.1021/acs.orglett.0c01626

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A chiral Al(III)-N,N'-dioxide complex catalyzes an acyloin rearrangement of cyclic α-ketols to provide an array of optically active 2-acyl-2-hydroxy cyclohexanones in good yields with high enantioselectivities. Asymmetric isomerizations of acyclic α-hydroxy aldehydes and α-iminols were achieved as well under modified conditions.

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Key Words

cyclohexanones, ring expansions

ID: J54-Y2020