Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins

[Image: see text] Enantioselective [2 + 2] cycloaddition of C(1)-ammonium enolates generated catalytically using the isothiourea HyperBTM with N-alkyl isatins gives spirocyclic β-lactones. In situ ring opening with an amine nucleophile generates isolable highly enantioenriched products in up to 92:8...

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Autores principales: Abdelhamid, Yusra, Kasten, Kevin, Dunne, Joanne, Hartley, Will C., Young, Claire M., Cordes, David B., Slawin, Alexandra M. Z., Ng, Sean, Smith, Andrew D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490795/
https://www.ncbi.nlm.nih.gov/pubmed/35848722
http://dx.doi.org/10.1021/acs.orglett.2c02170
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author Abdelhamid, Yusra
Kasten, Kevin
Dunne, Joanne
Hartley, Will C.
Young, Claire M.
Cordes, David B.
Slawin, Alexandra M. Z.
Ng, Sean
Smith, Andrew D.
author_facet Abdelhamid, Yusra
Kasten, Kevin
Dunne, Joanne
Hartley, Will C.
Young, Claire M.
Cordes, David B.
Slawin, Alexandra M. Z.
Ng, Sean
Smith, Andrew D.
author_sort Abdelhamid, Yusra
collection PubMed
description [Image: see text] Enantioselective [2 + 2] cycloaddition of C(1)-ammonium enolates generated catalytically using the isothiourea HyperBTM with N-alkyl isatins gives spirocyclic β-lactones. In situ ring opening with an amine nucleophile generates isolable highly enantioenriched products in up to 92:8 dr and in >99:1 er.
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spelling pubmed-94907952022-09-22 Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins Abdelhamid, Yusra Kasten, Kevin Dunne, Joanne Hartley, Will C. Young, Claire M. Cordes, David B. Slawin, Alexandra M. Z. Ng, Sean Smith, Andrew D. Org Lett [Image: see text] Enantioselective [2 + 2] cycloaddition of C(1)-ammonium enolates generated catalytically using the isothiourea HyperBTM with N-alkyl isatins gives spirocyclic β-lactones. In situ ring opening with an amine nucleophile generates isolable highly enantioenriched products in up to 92:8 dr and in >99:1 er. American Chemical Society 2022-07-18 2022-07-29 /pmc/articles/PMC9490795/ /pubmed/35848722 http://dx.doi.org/10.1021/acs.orglett.2c02170 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Abdelhamid, Yusra
Kasten, Kevin
Dunne, Joanne
Hartley, Will C.
Young, Claire M.
Cordes, David B.
Slawin, Alexandra M. Z.
Ng, Sean
Smith, Andrew D.
Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins
title Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins
title_full Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins
title_fullStr Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins
title_full_unstemmed Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins
title_short Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins
title_sort isothiourea-catalyzed [2 + 2] cycloaddition of c(1)-ammonium enolates and n-alkyl isatins
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9490795/
https://www.ncbi.nlm.nih.gov/pubmed/35848722
http://dx.doi.org/10.1021/acs.orglett.2c02170
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