Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions

[Image: see text] An enantioselective domino Michael–Michael reaction of nitroolefins and 2-nitro-3-arylacrylates has been established, which provided a series of spirocyclopentane oxindoles with four consecutive stereocenters including quaternary α-nitro esters with good yields (up to 73%) and exce...

Descripción completa

Detalles Bibliográficos
Autores principales: Chaudhari, Prakash D., Hong, Bor-Cherng, Wen, Chao-Lin, Lee, Gene-Hsiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648780/
https://www.ncbi.nlm.nih.gov/pubmed/31459355
http://dx.doi.org/10.1021/acsomega.8b03049
_version_ 1783437941330149376
author Chaudhari, Prakash D.
Hong, Bor-Cherng
Wen, Chao-Lin
Lee, Gene-Hsiang
author_facet Chaudhari, Prakash D.
Hong, Bor-Cherng
Wen, Chao-Lin
Lee, Gene-Hsiang
author_sort Chaudhari, Prakash D.
collection PubMed
description [Image: see text] An enantioselective domino Michael–Michael reaction of nitroolefins and 2-nitro-3-arylacrylates has been established, which provided a series of spirocyclopentane oxindoles with four consecutive stereocenters including quaternary α-nitro esters with good yields (up to 73%) and excellent enantioselectivities (up to 97% ee). The reaction was realized and optimized with the aid of a chiral squaramide-amine catalyst. The structures of 11 products were confirmed by single-crystal X-ray diffraction analysis.
format Online
Article
Text
id pubmed-6648780
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-66487802019-08-27 Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions Chaudhari, Prakash D. Hong, Bor-Cherng Wen, Chao-Lin Lee, Gene-Hsiang ACS Omega [Image: see text] An enantioselective domino Michael–Michael reaction of nitroolefins and 2-nitro-3-arylacrylates has been established, which provided a series of spirocyclopentane oxindoles with four consecutive stereocenters including quaternary α-nitro esters with good yields (up to 73%) and excellent enantioselectivities (up to 97% ee). The reaction was realized and optimized with the aid of a chiral squaramide-amine catalyst. The structures of 11 products were confirmed by single-crystal X-ray diffraction analysis. American Chemical Society 2019-01-09 /pmc/articles/PMC6648780/ /pubmed/31459355 http://dx.doi.org/10.1021/acsomega.8b03049 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Chaudhari, Prakash D.
Hong, Bor-Cherng
Wen, Chao-Lin
Lee, Gene-Hsiang
Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions
title Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions
title_full Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions
title_fullStr Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions
title_full_unstemmed Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions
title_short Asymmetric Synthesis of Spirocyclopentane Oxindoles Containing Four Consecutive Stereocenters and Quaternary α-Nitro Esters via Organocatalytic Enantioselective Michael–Michael Cascade Reactions
title_sort asymmetric synthesis of spirocyclopentane oxindoles containing four consecutive stereocenters and quaternary α-nitro esters via organocatalytic enantioselective michael–michael cascade reactions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648780/
https://www.ncbi.nlm.nih.gov/pubmed/31459355
http://dx.doi.org/10.1021/acsomega.8b03049
work_keys_str_mv AT chaudhariprakashd asymmetricsynthesisofspirocyclopentaneoxindolescontainingfourconsecutivestereocentersandquaternaryanitroestersviaorganocatalyticenantioselectivemichaelmichaelcascadereactions
AT hongborcherng asymmetricsynthesisofspirocyclopentaneoxindolescontainingfourconsecutivestereocentersandquaternaryanitroestersviaorganocatalyticenantioselectivemichaelmichaelcascadereactions
AT wenchaolin asymmetricsynthesisofspirocyclopentaneoxindolescontainingfourconsecutivestereocentersandquaternaryanitroestersviaorganocatalyticenantioselectivemichaelmichaelcascadereactions
AT leegenehsiang asymmetricsynthesisofspirocyclopentaneoxindolescontainingfourconsecutivestereocentersandquaternaryanitroestersviaorganocatalyticenantioselectivemichaelmichaelcascadereactions

Ejemplares similares