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Tandem Insertion–[1,3]‐Rearrangement: Highly Enantioselective Construction of α‐Aminoketones
Author(s) -
Chen Yushuang,
Liu Yun,
Li Zhaojing,
Dong Shunxi,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201914645
Subject(s) - enantioselective synthesis , chemistry , sulfonium , rhodium , rearrangement reaction , tandem , stereochemistry , catalysis , cope rearrangement , carroll rearrangement , ether , migratory insertion , combinatorial chemistry , medicinal chemistry , salt (chemistry) , claisen rearrangement , organic chemistry , materials science , composite material
An enantioselective synthesis of α‐aminoketone derivatives were readily available through 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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