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卷 25, 期 17, 页码 3126-3130出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c00986
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Enantioselective synthesis of alpha-chlorinated carboxylic acid esters was achieved with er up to 99:1 and yields up to 82% via a one-pot multistep protocol starting from alpha-diazoketones. This process involves a photochemical Wolff rearrangement, enantioselective alpha-chlorination using a chiral Lewis base catalyst, and a final nucleophilic displacement of the bound catalyst. The resulting products were successfully used for stereospecific nucleophilic displacement reactions with N- and S-nucleophiles.
The enantioselective synthesis of alpha-chlorinated carboxylic acid esters with er up to 99:1 and yields up to 82% was achieved via a one-pot multistep protocol starting from alpha-diazoketones. This process proceeds via a photochemical Wolff rearrangement, trapping of the generated ketene with a chiral Lewis base catalyst, subsequent enantioselective alpha-chlorination, and a final nucleophilic displacement of the bound catalyst. The obtained products were successfully utilized for stereospecific nucleophilic displacement reactions with N-and S-nucleophiles.
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