General and Efficient Copper-Catalyzed Oxazaborolidine Complex in Transfer Hydrogenation of Isoquinolines under Mild Conditions

[Image: see text] A general and efficient method for copper-catalyzed transfer hydrogenation of isoquinolines with an oxazaborolidine–BH(3) complex, under mild reaction conditions, is successfully developed. A broad range of isoquinolines has been reduced to the corresponding products with 61–85% yi...

Descripción completa

Detalles Bibliográficos
Autores principales: Du, Qianyu, Liu, Linpeng, Zhou, Taigang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7450644/
https://www.ncbi.nlm.nih.gov/pubmed/32875258
http://dx.doi.org/10.1021/acsomega.0c02957
_version_ 1783574845180608512
author Du, Qianyu
Liu, Linpeng
Zhou, Taigang
author_facet Du, Qianyu
Liu, Linpeng
Zhou, Taigang
author_sort Du, Qianyu
collection PubMed
description [Image: see text] A general and efficient method for copper-catalyzed transfer hydrogenation of isoquinolines with an oxazaborolidine–BH(3) complex, under mild reaction conditions, is successfully developed. A broad range of isoquinolines has been reduced to the corresponding products with 61–85% yields. The method is applied to the synthesis of biologically active tetrahydrosioquinoline alkaloid (±)-norlaudanosine in 62% yield, which is the key precursor for the preparation of (±)-laudanosine, (±)-N-methyl-laudanosine, and (±)-xylopinine in one or two steps.
format Online
Article
Text
id pubmed-7450644
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-74506442020-08-31 General and Efficient Copper-Catalyzed Oxazaborolidine Complex in Transfer Hydrogenation of Isoquinolines under Mild Conditions Du, Qianyu Liu, Linpeng Zhou, Taigang ACS Omega [Image: see text] A general and efficient method for copper-catalyzed transfer hydrogenation of isoquinolines with an oxazaborolidine–BH(3) complex, under mild reaction conditions, is successfully developed. A broad range of isoquinolines has been reduced to the corresponding products with 61–85% yields. The method is applied to the synthesis of biologically active tetrahydrosioquinoline alkaloid (±)-norlaudanosine in 62% yield, which is the key precursor for the preparation of (±)-laudanosine, (±)-N-methyl-laudanosine, and (±)-xylopinine in one or two steps. American Chemical Society 2020-08-13 /pmc/articles/PMC7450644/ /pubmed/32875258 http://dx.doi.org/10.1021/acsomega.0c02957 Text en Copyright © 2020 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 Du, Qianyu
Liu, Linpeng
Zhou, Taigang
General and Efficient Copper-Catalyzed Oxazaborolidine Complex in Transfer Hydrogenation of Isoquinolines under Mild Conditions
title General and Efficient Copper-Catalyzed Oxazaborolidine Complex in Transfer Hydrogenation of Isoquinolines under Mild Conditions
title_full General and Efficient Copper-Catalyzed Oxazaborolidine Complex in Transfer Hydrogenation of Isoquinolines under Mild Conditions
title_fullStr General and Efficient Copper-Catalyzed Oxazaborolidine Complex in Transfer Hydrogenation of Isoquinolines under Mild Conditions
title_full_unstemmed General and Efficient Copper-Catalyzed Oxazaborolidine Complex in Transfer Hydrogenation of Isoquinolines under Mild Conditions
title_short General and Efficient Copper-Catalyzed Oxazaborolidine Complex in Transfer Hydrogenation of Isoquinolines under Mild Conditions
title_sort general and efficient copper-catalyzed oxazaborolidine complex in transfer hydrogenation of isoquinolines under mild conditions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7450644/
https://www.ncbi.nlm.nih.gov/pubmed/32875258
http://dx.doi.org/10.1021/acsomega.0c02957
work_keys_str_mv AT duqianyu generalandefficientcoppercatalyzedoxazaborolidinecomplexintransferhydrogenationofisoquinolinesundermildconditions
AT liulinpeng generalandefficientcoppercatalyzedoxazaborolidinecomplexintransferhydrogenationofisoquinolinesundermildconditions
AT zhoutaigang generalandefficientcoppercatalyzedoxazaborolidinecomplexintransferhydrogenationofisoquinolinesundermildconditions

Ejemplares similares