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Asymmetric Aza-Claisen Rearrangement between Enantioenriched α-Chiral Allylamines and Allenones

Rui-Han Dai, Qi Wang, Zhi-Xiong Chen and Shi-Kai Tian*

*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China, Email: tianskustc.edu.cn

R.-H. Dai, Q. Wang, Z.-X. Chen, S.-K. Tian, J. Org. Chem., 2021, 86, 3065-3073.

DOI: 10.1021/acs.joc.0c02832



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Abstract

An unprecedented asymmetric aza-Claisen rearrangement between enantioenriched α-chiral allylamines and allenones provides - followed by hydrolysis - structurally diverse δ-chiral β-diketones in good to excellent yields with excellent retention of enantiopurity. This protocol enabled the construction of an all-carbon quaternary stereocenter with high enantiopurity.

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proposed mechanism



Key Words

Claisen Rearrangement, allylation, hydrolysis


ID: J42-Y2021