Cargando…

Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization

[Image: see text] Nickel-catalyzed additions of arylboronic acids to alkynes, followed by enantioselective cyclizations of the alkenylnickel species onto tethered ketones or enones, are reported. These reactions are reliant upon the formal anti-carbonickelation of the alkyne, which is postulated to...

Descripción completa

Detalles Bibliográficos
Autores principales: Clarke, Christopher, Incerti-Pradillos, Celia A., Lam, Hon Wai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4957849/
https://www.ncbi.nlm.nih.gov/pubmed/27333360
http://dx.doi.org/10.1021/jacs.6b04206
_version_ 1782444236677840896
author Clarke, Christopher
Incerti-Pradillos, Celia A.
Lam, Hon Wai
author_facet Clarke, Christopher
Incerti-Pradillos, Celia A.
Lam, Hon Wai
author_sort Clarke, Christopher
collection PubMed
description [Image: see text] Nickel-catalyzed additions of arylboronic acids to alkynes, followed by enantioselective cyclizations of the alkenylnickel species onto tethered ketones or enones, are reported. These reactions are reliant upon the formal anti-carbonickelation of the alkyne, which is postulated to occur by the reversible E/Z isomerization of an alkenylnickel species.
format Online
Article
Text
id pubmed-4957849
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-49578492016-07-25 Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization Clarke, Christopher Incerti-Pradillos, Celia A. Lam, Hon Wai J Am Chem Soc [Image: see text] Nickel-catalyzed additions of arylboronic acids to alkynes, followed by enantioselective cyclizations of the alkenylnickel species onto tethered ketones or enones, are reported. These reactions are reliant upon the formal anti-carbonickelation of the alkyne, which is postulated to occur by the reversible E/Z isomerization of an alkenylnickel species. American Chemical Society 2016-06-22 2016-07-06 /pmc/articles/PMC4957849/ /pubmed/27333360 http://dx.doi.org/10.1021/jacs.6b04206 Text en Copyright © 2016 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Clarke, Christopher
Incerti-Pradillos, Celia A.
Lam, Hon Wai
Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization
title Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization
title_full Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization
title_fullStr Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization
title_full_unstemmed Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization
title_short Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization
title_sort enantioselective nickel-catalyzed anti-carbometallative cyclizations of alkynyl electrophiles enabled by reversible alkenylnickel e/z isomerization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4957849/
https://www.ncbi.nlm.nih.gov/pubmed/27333360
http://dx.doi.org/10.1021/jacs.6b04206
work_keys_str_mv AT clarkechristopher enantioselectivenickelcatalyzedanticarbometallativecyclizationsofalkynylelectrophilesenabledbyreversiblealkenylnickelezisomerization
AT incertipradillosceliaa enantioselectivenickelcatalyzedanticarbometallativecyclizationsofalkynylelectrophilesenabledbyreversiblealkenylnickelezisomerization
AT lamhonwai enantioselectivenickelcatalyzedanticarbometallativecyclizationsofalkynylelectrophilesenabledbyreversiblealkenylnickelezisomerization