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Synthesis 2018; 50(19): 3936-3946
DOI: 10.1055/s-0037-1610440
DOI: 10.1055/s-0037-1610440
paper
Sulfonamides as Amine Component in the Petasis-Borono Mannich Reaction: A Concise Synthesis of α-Aryl- and α-Alkenylglycine Derivatives
This work was financially supported by the Fonds der Chemischen Industrie (Liebig Fellowship to G. M.).
Further Information
Publication History
Received: 13 April 2018
Accepted after revision: 30 May 2018
Publication Date:
18 July 2018 (online)
Abstract
A catalyst-free three-component synthesis of α-aryl- and α-alkenylglycine derivatives starting from glyoxylic acid, sulfonamides, and aryl- or alkenylboronic acids is described. This operationally simple method tolerates a broad range of functional groups and enables the generation of a wide array of α-amino acids. Sulfonamides were utilized as amine component in the classic Petasis reaction for the first time.
Key words
multicomponent reaction - Petasis-borono Mannich reaction - sulfonamides - amino acids - catalyst freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610440.
- Supporting Information
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For synthesis of the sulfonamides, see:
For synthesis of the arylboronic acids, see: