Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist

First catalytic and enantioselective conjugate addition of nitromethane to benzylidene-2-benzoyl acetate has been developed using dihydroquinine derived squaramide catalyst with moderate to high selectivities. Asymmetric total synthesis of ABT-627, a potent ETA receptor antagonist is accomplished ut...

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Autores principales: Hajra, Saumen, Aziz, Sk Mohammad, Jana, Bibekananda, Hazra, Sunit
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7066299/
https://www.ncbi.nlm.nih.gov/pubmed/32195223
http://dx.doi.org/10.3389/fchem.2020.00135
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author Hajra, Saumen
Aziz, Sk Mohammad
Jana, Bibekananda
Hazra, Sunit
author_facet Hajra, Saumen
Aziz, Sk Mohammad
Jana, Bibekananda
Hazra, Sunit
author_sort Hajra, Saumen
collection PubMed
description First catalytic and enantioselective conjugate addition of nitromethane to benzylidene-2-benzoyl acetate has been developed using dihydroquinine derived squaramide catalyst with moderate to high selectivities. Asymmetric total synthesis of ABT-627, a potent ETA receptor antagonist is accomplished utilizing the developed method in overall 15.7% yield.
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spelling pubmed-70662992020-03-19 Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist Hajra, Saumen Aziz, Sk Mohammad Jana, Bibekananda Hazra, Sunit Front Chem Chemistry First catalytic and enantioselective conjugate addition of nitromethane to benzylidene-2-benzoyl acetate has been developed using dihydroquinine derived squaramide catalyst with moderate to high selectivities. Asymmetric total synthesis of ABT-627, a potent ETA receptor antagonist is accomplished utilizing the developed method in overall 15.7% yield. Frontiers Media S.A. 2020-03-05 /pmc/articles/PMC7066299/ /pubmed/32195223 http://dx.doi.org/10.3389/fchem.2020.00135 Text en Copyright © 2020 Hajra, Aziz, Jana and Hazra. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Hajra, Saumen
Aziz, Sk Mohammad
Jana, Bibekananda
Hazra, Sunit
Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist
title Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist
title_full Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist
title_fullStr Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist
title_full_unstemmed Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist
title_short Organocatalytic Enantioselective Conjugate Addition of Nitromethane to Benzylidene-2-Benzoyl Acetate: Asymmetric Synthesis of ABT – 627, an Endothelin Receptor Antagonist
title_sort organocatalytic enantioselective conjugate addition of nitromethane to benzylidene-2-benzoyl acetate: asymmetric synthesis of abt – 627, an endothelin receptor antagonist
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7066299/
https://www.ncbi.nlm.nih.gov/pubmed/32195223
http://dx.doi.org/10.3389/fchem.2020.00135
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