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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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
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author Srinivasulu, Chinthaginjala
Sagar, Nagamangala R.
Vishwanatha, Thimmalapura M.
Durgamma, Suram
Sureshbabu, Vommina V.
author_facet Srinivasulu, Chinthaginjala
Sagar, Nagamangala R.
Vishwanatha, Thimmalapura M.
Durgamma, Suram
Sureshbabu, Vommina V.
author_sort Srinivasulu, Chinthaginjala
collection PubMed
description [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.
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spelling pubmed-79058282021-02-26 Synthesis of N(β)-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol Srinivasulu, Chinthaginjala Sagar, Nagamangala R. Vishwanatha, Thimmalapura M. Durgamma, Suram Sureshbabu, Vommina V. ACS Omega [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. American Chemical Society 2021-02-10 /pmc/articles/PMC7905828/ /pubmed/33644575 http://dx.doi.org/10.1021/acsomega.0c05419 Text en © 2021 The Authors. Published by American Chemical Society Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Srinivasulu, Chinthaginjala
Sagar, Nagamangala R.
Vishwanatha, Thimmalapura M.
Durgamma, Suram
Sureshbabu, Vommina V.
Synthesis of N(β)-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol
title Synthesis of N(β)-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol
title_full Synthesis of N(β)-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol
title_fullStr Synthesis of N(β)-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol
title_full_unstemmed Synthesis of N(β)-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol
title_short Synthesis of N(β)-Protected Amino Sulfenyl Methyl Formamides and Sulfonyl Methyl Formamides: A Simple Protocol
title_sort synthesis of n(β)-protected amino sulfenyl methyl formamides and sulfonyl methyl formamides: a simple protocol
url 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
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