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Tandem Insertion/[1,3]-rearrangement: Highly Enantioselective Construction Of α-Aminoketones.

Yushuang Chen, Y. Liu, Zhaojing Li, S. Dong, X. Liu, X. Feng
Published 2020 · Chemistry, Medicine

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An enantioselective synthesis of α -aminoketone derivatives were readily available via a tandem insertion/[1,3] O-to-C rearrangement reaction. The rhodium salt and chiral N,N ' -dioxide-indium(III) complex make up relay catalysis, which enables the O-H insertion of benzylic alcohols to N -sulfonyl-1,2,3-triazoles, and asymmetric [1,3]-rearrangement of amino enol ether intermediates, subsequently. Preliminary mechanistic studies suggested that the [1,3] O-to-C rearrangement step proceeded through an ion pair pathway.
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