One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis

[Image: see text] The highly enantioselective preparation of trisubstituted pyrrolidine derivatives employing a one-pot nitro-Mannich/hydroamination cascade is reported. This cascade approach utilizes an asymmetric bifunctional organocatalytic nitro-Mannich reaction followed by a gold-catalyzed alle...

Descripción completa

Detalles Bibliográficos
Autores principales: Barber, David M., Ďuriš, Andrej, Thompson, Amber L., Sanganee, Hitesh J., Dixon, Darren J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3931436/
https://www.ncbi.nlm.nih.gov/pubmed/24563809
http://dx.doi.org/10.1021/cs401008v
_version_ 1782304662815244288
author Barber, David M.
Ďuriš, Andrej
Thompson, Amber L.
Sanganee, Hitesh J.
Dixon, Darren J.
author_facet Barber, David M.
Ďuriš, Andrej
Thompson, Amber L.
Sanganee, Hitesh J.
Dixon, Darren J.
author_sort Barber, David M.
collection PubMed
description [Image: see text] The highly enantioselective preparation of trisubstituted pyrrolidine derivatives employing a one-pot nitro-Mannich/hydroamination cascade is reported. This cascade approach utilizes an asymmetric bifunctional organocatalytic nitro-Mannich reaction followed by a gold-catalyzed allene hydroamination reaction. The products are afforded in good yields and excellent diastereo- and enantioselectivities.
format Online
Article
Text
id pubmed-3931436
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-39314362014-02-21 One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis Barber, David M. Ďuriš, Andrej Thompson, Amber L. Sanganee, Hitesh J. Dixon, Darren J. ACS Catal [Image: see text] The highly enantioselective preparation of trisubstituted pyrrolidine derivatives employing a one-pot nitro-Mannich/hydroamination cascade is reported. This cascade approach utilizes an asymmetric bifunctional organocatalytic nitro-Mannich reaction followed by a gold-catalyzed allene hydroamination reaction. The products are afforded in good yields and excellent diastereo- and enantioselectivities. American Chemical Society 2014-01-06 2014-02-07 /pmc/articles/PMC3931436/ /pubmed/24563809 http://dx.doi.org/10.1021/cs401008v Text en Copyright © 2014 American Chemical Society
spellingShingle Barber, David M.
Ďuriš, Andrej
Thompson, Amber L.
Sanganee, Hitesh J.
Dixon, Darren J.
One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis
title One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis
title_full One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis
title_fullStr One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis
title_full_unstemmed One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis
title_short One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis
title_sort one-pot asymmetric nitro-mannich/hydroamination cascades for the synthesis of pyrrolidine derivatives: combining organocatalysis and gold catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3931436/
https://www.ncbi.nlm.nih.gov/pubmed/24563809
http://dx.doi.org/10.1021/cs401008v
work_keys_str_mv AT barberdavidm onepotasymmetricnitromannichhydroaminationcascadesforthesynthesisofpyrrolidinederivativescombiningorganocatalysisandgoldcatalysis
AT durisandrej onepotasymmetricnitromannichhydroaminationcascadesforthesynthesisofpyrrolidinederivativescombiningorganocatalysisandgoldcatalysis
AT thompsonamberl onepotasymmetricnitromannichhydroaminationcascadesforthesynthesisofpyrrolidinederivativescombiningorganocatalysisandgoldcatalysis
AT sanganeehiteshj onepotasymmetricnitromannichhydroaminationcascadesforthesynthesisofpyrrolidinederivativescombiningorganocatalysisandgoldcatalysis
AT dixondarrenj onepotasymmetricnitromannichhydroaminationcascadesforthesynthesisofpyrrolidinederivativescombiningorganocatalysisandgoldcatalysis

Ejemplares similares