Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis

[Image: see text] Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid. The reaction provides high yields and excellent stereocontrol in the formation of complex adducts with one or two α-tertiary amine moi...

Descripción completa

Detalles Bibliográficos
Autores principales: Sendra, Jana, Reyes, Efraim, Prieto, Liher, Fernández, Elena, Vicario, Jose L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8609578/
https://www.ncbi.nlm.nih.gov/pubmed/34726408
http://dx.doi.org/10.1021/acs.orglett.1c03190
_version_ 1784602945298366464
author Sendra, Jana
Reyes, Efraim
Prieto, Liher
Fernández, Elena
Vicario, Jose L.
author_facet Sendra, Jana
Reyes, Efraim
Prieto, Liher
Fernández, Elena
Vicario, Jose L.
author_sort Sendra, Jana
collection PubMed
description [Image: see text] Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid. The reaction provides high yields and excellent stereocontrol in the formation of complex adducts with one or two α-tertiary amine moieties at the ring fusion, and these can be converted into very versatile stereodefined decalin- or octahydro-1H-indene-derived 1,3-diamines through simple reductive N–N cleavage.
format Online
Article
Text
id pubmed-8609578
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-86095782021-11-24 Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis Sendra, Jana Reyes, Efraim Prieto, Liher Fernández, Elena Vicario, Jose L. Org Lett [Image: see text] Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid. The reaction provides high yields and excellent stereocontrol in the formation of complex adducts with one or two α-tertiary amine moieties at the ring fusion, and these can be converted into very versatile stereodefined decalin- or octahydro-1H-indene-derived 1,3-diamines through simple reductive N–N cleavage. American Chemical Society 2021-11-02 2021-11-19 /pmc/articles/PMC8609578/ /pubmed/34726408 http://dx.doi.org/10.1021/acs.orglett.1c03190 Text en © 2021 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 Sendra, Jana
Reyes, Efraim
Prieto, Liher
Fernández, Elena
Vicario, Jose L.
Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis
title Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis
title_full Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis
title_fullStr Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis
title_full_unstemmed Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis
title_short Transannular Enantioselective (3 + 2) Cycloaddition of Cycloalkenone Hydrazones under Brønsted Acid Catalysis
title_sort transannular enantioselective (3 + 2) cycloaddition of cycloalkenone hydrazones under brønsted acid catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8609578/
https://www.ncbi.nlm.nih.gov/pubmed/34726408
http://dx.doi.org/10.1021/acs.orglett.1c03190
work_keys_str_mv AT sendrajana transannularenantioselective32cycloadditionofcycloalkenonehydrazonesunderbrønstedacidcatalysis
AT reyesefraim transannularenantioselective32cycloadditionofcycloalkenonehydrazonesunderbrønstedacidcatalysis
AT prietoliher transannularenantioselective32cycloadditionofcycloalkenonehydrazonesunderbrønstedacidcatalysis
AT fernandezelena transannularenantioselective32cycloadditionofcycloalkenonehydrazonesunderbrønstedacidcatalysis
AT vicariojosel transannularenantioselective32cycloadditionofcycloalkenonehydrazonesunderbrønstedacidcatalysis

Ejemplares similares