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Synthesis of N(β)-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol

[Image: see text] Chiral amino acid-derived formamides represent one of the most versatile components in multicomponent reactions. Herein, we describe a facile synthesis of N(β)-protected amino sulfenyl methyl formamides and sulfonyl methyl formamides via the Mannich reaction of N(α)-protected amino...

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Detalles Bibliográficos
Autores principales: Srinivasulu, Chinthaginjala, Sagar, Nagamangala R., Vishwanatha, Thimmalapura M., Durgamma, Suram, Sureshbabu, Vommina V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7905828/
https://www.ncbi.nlm.nih.gov/pubmed/33644575
http://dx.doi.org/10.1021/acsomega.0c05419
Descripción
Sumario:[Image: see text] Chiral amino acid-derived formamides represent one of the most versatile components in multicomponent reactions. Herein, we describe a facile synthesis of N(β)-protected amino sulfenyl methyl formamides and sulfonyl methyl formamides via the Mannich reaction of N(α)-protected amino alkyl thiols followed by oxidation using 3-chloroperbenzoic acid (m-CPBA). This protocol is applicable to a wide range of Fmoc- and Cbz-protected amino acids. Notably, the reaction provides high yield and retains the stereochemistry of the chiral center of the starting component.