Catalyst-free nitration of the aliphatic C-H bonds of tertiary beta-keto esters with tert-butyl nitrite: Access to alpha-quaternary alpha-amino acid precursors
Catalyst-free nitration of the aliphatic C-H bonds of tertiary beta-keto esters with tert-butyl nitrite: Access to alpha-quaternary alpha-amino acid precursors
An efficient catalyst-free direct nitration of the C-H bonds of tertiary beta-keto esters using tert-butyl nitrite as a nitrating reagent is described. This radical nitration protocol tolerants diverse functional groups, leading to the preparation of linear and cyclic alpha-nitro-beta-keto ester derivatives in good to excellent yields under mild conditions. In addition, the nitration product 3a was applied to the concise synthesis of a quaternary alpha-amino acid 4 in the presence of zinc power and acetic acid. (C) 2022 Elsevier Ltd. All rights reserved.
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