Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi–Joullié reaction

Starting from easily accessible chiral enantiopure 1,2-amino alcohols and salicylaldehydes, a concise route to cyclic imines has been developed. These chiral cyclic imines undergo a highly diastereoselective Ugi–Joullié reaction to give trans tetrahydrobenzo[f][1,4]oxazepines with the introduction o...

Descripción completa

Detalles Bibliográficos
Autores principales: Pinna, Alessandro, Basso, Andrea, Lambruschini, Chiara, Moni, Lisa, Riva, Renata, Rocca, Valeria, Banfi, Luca
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9047508/
https://www.ncbi.nlm.nih.gov/pubmed/35494435
http://dx.doi.org/10.1039/c9ra10689h
_version_ 1784695742807408640
author Pinna, Alessandro
Basso, Andrea
Lambruschini, Chiara
Moni, Lisa
Riva, Renata
Rocca, Valeria
Banfi, Luca
author_facet Pinna, Alessandro
Basso, Andrea
Lambruschini, Chiara
Moni, Lisa
Riva, Renata
Rocca, Valeria
Banfi, Luca
author_sort Pinna, Alessandro
collection PubMed
description Starting from easily accessible chiral enantiopure 1,2-amino alcohols and salicylaldehydes, a concise route to cyclic imines has been developed. These chiral cyclic imines undergo a highly diastereoselective Ugi–Joullié reaction to give trans tetrahydrobenzo[f][1,4]oxazepines with the introduction of up to 4 diversity inputs. The cis isomer may also be attained, thanks to a thermodynamically controlled base catalysed epimerization. Free secondary amines have been obtained using an unprecedented “removable” carboxylic acid.
format Online
Article
Text
id pubmed-9047508
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90475082022-04-28 Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi–Joullié reaction Pinna, Alessandro Basso, Andrea Lambruschini, Chiara Moni, Lisa Riva, Renata Rocca, Valeria Banfi, Luca RSC Adv Chemistry Starting from easily accessible chiral enantiopure 1,2-amino alcohols and salicylaldehydes, a concise route to cyclic imines has been developed. These chiral cyclic imines undergo a highly diastereoselective Ugi–Joullié reaction to give trans tetrahydrobenzo[f][1,4]oxazepines with the introduction of up to 4 diversity inputs. The cis isomer may also be attained, thanks to a thermodynamically controlled base catalysed epimerization. Free secondary amines have been obtained using an unprecedented “removable” carboxylic acid. The Royal Society of Chemistry 2020-01-03 /pmc/articles/PMC9047508/ /pubmed/35494435 http://dx.doi.org/10.1039/c9ra10689h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Pinna, Alessandro
Basso, Andrea
Lambruschini, Chiara
Moni, Lisa
Riva, Renata
Rocca, Valeria
Banfi, Luca
Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi–Joullié reaction
title Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi–Joullié reaction
title_full Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi–Joullié reaction
title_fullStr Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi–Joullié reaction
title_full_unstemmed Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi–Joullié reaction
title_short Stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent Ugi–Joullié reaction
title_sort stereodivergent access to all four stereoisomers of chiral tetrahydrobenzo[f][1,4]oxazepines, through highly diastereoselective multicomponent ugi–joullié reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9047508/
https://www.ncbi.nlm.nih.gov/pubmed/35494435
http://dx.doi.org/10.1039/c9ra10689h
work_keys_str_mv AT pinnaalessandro stereodivergentaccesstoallfourstereoisomersofchiraltetrahydrobenzof14oxazepinesthroughhighlydiastereoselectivemulticomponentugijoulliereaction
AT bassoandrea stereodivergentaccesstoallfourstereoisomersofchiraltetrahydrobenzof14oxazepinesthroughhighlydiastereoselectivemulticomponentugijoulliereaction
AT lambruschinichiara stereodivergentaccesstoallfourstereoisomersofchiraltetrahydrobenzof14oxazepinesthroughhighlydiastereoselectivemulticomponentugijoulliereaction
AT monilisa stereodivergentaccesstoallfourstereoisomersofchiraltetrahydrobenzof14oxazepinesthroughhighlydiastereoselectivemulticomponentugijoulliereaction
AT rivarenata stereodivergentaccesstoallfourstereoisomersofchiraltetrahydrobenzof14oxazepinesthroughhighlydiastereoselectivemulticomponentugijoulliereaction
AT roccavaleria stereodivergentaccesstoallfourstereoisomersofchiraltetrahydrobenzof14oxazepinesthroughhighlydiastereoselectivemulticomponentugijoulliereaction
AT banfiluca stereodivergentaccesstoallfourstereoisomersofchiraltetrahydrobenzof14oxazepinesthroughhighlydiastereoselectivemulticomponentugijoulliereaction

Ejemplares similares