Umpolung Amide Synthesis Using Substoichiometric N-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant

[Image: see text] Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C–N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS)...

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Autores principales: Schwieter, Kenneth E., Shen, Bo, Shackleford, Jessica P., Leighty, Matthew W., Johnston, Jeffrey N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168777/
https://www.ncbi.nlm.nih.gov/pubmed/25198239
http://dx.doi.org/10.1021/ol502089v
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author Schwieter, Kenneth E.
Shen, Bo
Shackleford, Jessica P.
Leighty, Matthew W.
Johnston, Jeffrey N.
author_facet Schwieter, Kenneth E.
Shen, Bo
Shackleford, Jessica P.
Leighty, Matthew W.
Johnston, Jeffrey N.
author_sort Schwieter, Kenneth E.
collection PubMed
description [Image: see text] Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C–N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS) under aerobic conditions has been developed. In combination with the enantioselective preparation of α-bromo nitroalkane donors, this protocol realizes the goal of enantioselective α-amino amide and peptide synthesis based solely on catalytic methods.
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spelling pubmed-41687772015-09-08 Umpolung Amide Synthesis Using Substoichiometric N-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant Schwieter, Kenneth E. Shen, Bo Shackleford, Jessica P. Leighty, Matthew W. Johnston, Jeffrey N. Org Lett [Image: see text] Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C–N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS) under aerobic conditions has been developed. In combination with the enantioselective preparation of α-bromo nitroalkane donors, this protocol realizes the goal of enantioselective α-amino amide and peptide synthesis based solely on catalytic methods. American Chemical Society 2014-09-08 2014-09-19 /pmc/articles/PMC4168777/ /pubmed/25198239 http://dx.doi.org/10.1021/ol502089v Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Schwieter, Kenneth E.
Shen, Bo
Shackleford, Jessica P.
Leighty, Matthew W.
Johnston, Jeffrey N.
Umpolung Amide Synthesis Using Substoichiometric N-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant
title Umpolung Amide Synthesis Using Substoichiometric N-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant
title_full Umpolung Amide Synthesis Using Substoichiometric N-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant
title_fullStr Umpolung Amide Synthesis Using Substoichiometric N-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant
title_full_unstemmed Umpolung Amide Synthesis Using Substoichiometric N-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant
title_short Umpolung Amide Synthesis Using Substoichiometric N-Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant
title_sort umpolung amide synthesis using substoichiometric n-iodosuccinimide (nis) and oxygen as a terminal oxidant
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4168777/
https://www.ncbi.nlm.nih.gov/pubmed/25198239
http://dx.doi.org/10.1021/ol502089v
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