Cargando…

Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes

A copper-catalyzed asymmetric reductive allyl–allyl cross-coupling reaction of allenes with allylic phosphates wherein allenes were used as allylmetal surrogates has been achieved for the first time. This protocol provides an efficient and straightforward route to optically active 1,5-dienes in a hi...

Descripción completa

Detalles Bibliográficos
Autores principales: Xu, Guoxing, Fu, Bin, Zhao, Haiyan, Li, Yanfei, Zhang, Ge, Wang, Ying, Xiong, Tao, Zhang, Qian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6369434/
https://www.ncbi.nlm.nih.gov/pubmed/30842848
http://dx.doi.org/10.1039/c8sc04505d
_version_ 1783394191077801984
author Xu, Guoxing
Fu, Bin
Zhao, Haiyan
Li, Yanfei
Zhang, Ge
Wang, Ying
Xiong, Tao
Zhang, Qian
author_facet Xu, Guoxing
Fu, Bin
Zhao, Haiyan
Li, Yanfei
Zhang, Ge
Wang, Ying
Xiong, Tao
Zhang, Qian
author_sort Xu, Guoxing
collection PubMed
description A copper-catalyzed asymmetric reductive allyl–allyl cross-coupling reaction of allenes with allylic phosphates wherein allenes were used as allylmetal surrogates has been achieved for the first time. This protocol provides an efficient and straightforward route to optically active 1,5-dienes in a highly enantioselective and site-specific fashion. Furthermore, all-carbon quaternary stereogenic centers could also be constructed with this protocol. The versatility of the products is demonstrated through a diverse array of further transformations of the enantioenriched 1,5-dienes.
format Online
Article
Text
id pubmed-6369434
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-63694342019-03-06 Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes Xu, Guoxing Fu, Bin Zhao, Haiyan Li, Yanfei Zhang, Ge Wang, Ying Xiong, Tao Zhang, Qian Chem Sci Chemistry A copper-catalyzed asymmetric reductive allyl–allyl cross-coupling reaction of allenes with allylic phosphates wherein allenes were used as allylmetal surrogates has been achieved for the first time. This protocol provides an efficient and straightforward route to optically active 1,5-dienes in a highly enantioselective and site-specific fashion. Furthermore, all-carbon quaternary stereogenic centers could also be constructed with this protocol. The versatility of the products is demonstrated through a diverse array of further transformations of the enantioenriched 1,5-dienes. Royal Society of Chemistry 2018-12-04 /pmc/articles/PMC6369434/ /pubmed/30842848 http://dx.doi.org/10.1039/c8sc04505d Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Xu, Guoxing
Fu, Bin
Zhao, Haiyan
Li, Yanfei
Zhang, Ge
Wang, Ying
Xiong, Tao
Zhang, Qian
Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes
title Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes
title_full Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes
title_fullStr Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes
title_full_unstemmed Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes
title_short Enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes
title_sort enantioselective and site-specific copper-catalyzed reductive allyl–allyl cross-coupling of allenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6369434/
https://www.ncbi.nlm.nih.gov/pubmed/30842848
http://dx.doi.org/10.1039/c8sc04505d
work_keys_str_mv AT xuguoxing enantioselectiveandsitespecificcoppercatalyzedreductiveallylallylcrosscouplingofallenes
AT fubin enantioselectiveandsitespecificcoppercatalyzedreductiveallylallylcrosscouplingofallenes
AT zhaohaiyan enantioselectiveandsitespecificcoppercatalyzedreductiveallylallylcrosscouplingofallenes
AT liyanfei enantioselectiveandsitespecificcoppercatalyzedreductiveallylallylcrosscouplingofallenes
AT zhangge enantioselectiveandsitespecificcoppercatalyzedreductiveallylallylcrosscouplingofallenes
AT wangying enantioselectiveandsitespecificcoppercatalyzedreductiveallylallylcrosscouplingofallenes
AT xiongtao enantioselectiveandsitespecificcoppercatalyzedreductiveallylallylcrosscouplingofallenes
AT zhangqian enantioselectiveandsitespecificcoppercatalyzedreductiveallylallylcrosscouplingofallenes