Synthesis of Nβ-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol

Chinthaginjala Srinivasulu; Nagamangala R Sagar; Thimmalapura M Vishwanatha; Suram Durgamma; Vommina V Sureshbabu

doi:10.1021/acsomega.0c05419

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

ACS Omega. 2021 Feb 10;6(7):4680-4686. doi: 10.1021/acsomega.0c05419. eCollection 2021 Feb 23.

Authors

Chinthaginjala Srinivasulu¹, Nagamangala R Sagar¹, Thimmalapura M Vishwanatha¹, Suram Durgamma¹, Vommina V Sureshbabu¹

Affiliation

¹ Peptide Research Laboratory, Department of Chemistry, Jnana Bharathi, Bangalore University, Bengaluru 560056, India.

Abstract

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.