A Brønsted base-promoted diastereoselective dimerization of azlactones

A novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60–93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistr...

Descripción completa

Detalles Bibliográficos
Autores principales: Pinheiro, Danielle L J, Batista, Gabriel M F, de Castro, Pedro P, Flores, Leonã S, Andrade, Gustavo F S, Amarante, Giovanni W
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5753058/
https://www.ncbi.nlm.nih.gov/pubmed/29564003
http://dx.doi.org/10.3762/bjoc.13.264
_version_ 1783290197372305408
author Pinheiro, Danielle L J
Batista, Gabriel M F
de Castro, Pedro P
Flores, Leonã S
Andrade, Gustavo F S
Amarante, Giovanni W
author_facet Pinheiro, Danielle L J
Batista, Gabriel M F
de Castro, Pedro P
Flores, Leonã S
Andrade, Gustavo F S
Amarante, Giovanni W
author_sort Pinheiro, Danielle L J
collection PubMed
description A novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60–93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistry of the major dimer was assigned as being trans, by X-ray crystallographic analysis. The kinetic reaction profile was determined by using (1)H NMR reaction monitoring and revealed a second order overall kinetic profile. Furthermore, by employing this methodology, a diastereoselective total synthesis of a functionalized analogue of streptopyrrolidine was accomplished in 65% overall yield.
format Online
Article
Text
id pubmed-5753058
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-57530582018-03-21 A Brønsted base-promoted diastereoselective dimerization of azlactones Pinheiro, Danielle L J Batista, Gabriel M F de Castro, Pedro P Flores, Leonã S Andrade, Gustavo F S Amarante, Giovanni W Beilstein J Org Chem Letter A novel Brønsted base system for the diastereoselective dimerization of azlactones using trichloroacetate salts and acetonitrile has been developed. Desired products were obtained in good yields (60–93%) and with up to >19:1 dr after one hour of reaction. Additionally, the relative stereochemistry of the major dimer was assigned as being trans, by X-ray crystallographic analysis. The kinetic reaction profile was determined by using (1)H NMR reaction monitoring and revealed a second order overall kinetic profile. Furthermore, by employing this methodology, a diastereoselective total synthesis of a functionalized analogue of streptopyrrolidine was accomplished in 65% overall yield. Beilstein-Institut 2017-12-13 /pmc/articles/PMC5753058/ /pubmed/29564003 http://dx.doi.org/10.3762/bjoc.13.264 Text en Copyright © 2017, Pinheiro et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Pinheiro, Danielle L J
Batista, Gabriel M F
de Castro, Pedro P
Flores, Leonã S
Andrade, Gustavo F S
Amarante, Giovanni W
A Brønsted base-promoted diastereoselective dimerization of azlactones
title A Brønsted base-promoted diastereoselective dimerization of azlactones
title_full A Brønsted base-promoted diastereoselective dimerization of azlactones
title_fullStr A Brønsted base-promoted diastereoselective dimerization of azlactones
title_full_unstemmed A Brønsted base-promoted diastereoselective dimerization of azlactones
title_short A Brønsted base-promoted diastereoselective dimerization of azlactones
title_sort brønsted base-promoted diastereoselective dimerization of azlactones
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5753058/
https://www.ncbi.nlm.nih.gov/pubmed/29564003
http://dx.doi.org/10.3762/bjoc.13.264
work_keys_str_mv AT pinheirodaniellelj abrønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT batistagabrielmf abrønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT decastropedrop abrønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT floresleonas abrønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT andradegustavofs abrønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT amarantegiovanniw abrønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT pinheirodaniellelj brønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT batistagabrielmf brønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT decastropedrop brønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT floresleonas brønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT andradegustavofs brønstedbasepromoteddiastereoselectivedimerizationofazlactones
AT amarantegiovanniw brønstedbasepromoteddiastereoselectivedimerizationofazlactones

Ejemplares similares