Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones

[Image: see text] Alkenes have been discovered to be chelating groups to Zn(II), enforcing highly stereoselective additions of organozincs to β,γ-unsaturated ketones. (1)H NMR studies and DFT calculations provide support for this surprising chelation mode. The results expand the range of coordinatin...

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Autores principales: Raffier, Ludovic, Gutierrez, Osvaldo, Stanton, Gretchen R., Kozlowski, Marisa C., Walsh, Patrick J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4195513/
https://www.ncbi.nlm.nih.gov/pubmed/25328269
http://dx.doi.org/10.1021/om5007006
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author Raffier, Ludovic
Gutierrez, Osvaldo
Stanton, Gretchen R.
Kozlowski, Marisa C.
Walsh, Patrick J.
author_facet Raffier, Ludovic
Gutierrez, Osvaldo
Stanton, Gretchen R.
Kozlowski, Marisa C.
Walsh, Patrick J.
author_sort Raffier, Ludovic
collection PubMed
description [Image: see text] Alkenes have been discovered to be chelating groups to Zn(II), enforcing highly stereoselective additions of organozincs to β,γ-unsaturated ketones. (1)H NMR studies and DFT calculations provide support for this surprising chelation mode. The results expand the range of coordinating groups for chelation-controlled carbonyl additions from heteroatom Lewis bases to simple C–C double bonds, broadening the 60 year old paradigm.
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spelling pubmed-41955132015-09-09 Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones Raffier, Ludovic Gutierrez, Osvaldo Stanton, Gretchen R. Kozlowski, Marisa C. Walsh, Patrick J. Organometallics [Image: see text] Alkenes have been discovered to be chelating groups to Zn(II), enforcing highly stereoselective additions of organozincs to β,γ-unsaturated ketones. (1)H NMR studies and DFT calculations provide support for this surprising chelation mode. The results expand the range of coordinating groups for chelation-controlled carbonyl additions from heteroatom Lewis bases to simple C–C double bonds, broadening the 60 year old paradigm. American Chemical Society 2014-09-09 2014-10-13 /pmc/articles/PMC4195513/ /pubmed/25328269 http://dx.doi.org/10.1021/om5007006 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Raffier, Ludovic
Gutierrez, Osvaldo
Stanton, Gretchen R.
Kozlowski, Marisa C.
Walsh, Patrick J.
Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones
title Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones
title_full Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones
title_fullStr Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones
title_full_unstemmed Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones
title_short Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones
title_sort alkenes as chelating groups in diastereoselective additions of organometallics to ketones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4195513/
https://www.ncbi.nlm.nih.gov/pubmed/25328269
http://dx.doi.org/10.1021/om5007006
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