Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes

A catalytic methodology for the enantioselective addition of alkylzirconium reagents to aliphatic aldehydes is reported here. The versatile and readily accessible chiral Ph-BINMOL ligand, in the presence of Ti(O(i)Pr)(4) and a zinc salt, facilitates the reaction, which proceeds under mild conditions...

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Autores principales: Vaccari, Jade, González-Soria, María José, Carter, Nicholas, Maciá, Beatriz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8347741/
https://www.ncbi.nlm.nih.gov/pubmed/34361623
http://dx.doi.org/10.3390/molecules26154471
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author Vaccari, Jade
González-Soria, María José
Carter, Nicholas
Maciá, Beatriz
author_facet Vaccari, Jade
González-Soria, María José
Carter, Nicholas
Maciá, Beatriz
author_sort Vaccari, Jade
collection PubMed
description A catalytic methodology for the enantioselective addition of alkylzirconium reagents to aliphatic aldehydes is reported here. The versatile and readily accessible chiral Ph-BINMOL ligand, in the presence of Ti(O(i)Pr)(4) and a zinc salt, facilitates the reaction, which proceeds under mild conditions and is compatible with functionalized nucleophiles. The alkylzirconium reagents are conveniently generated in situ by hydrozirconation of alkenes with the Schwartz reagent. This work is a continuation of our previous work on aromatic aldehydes.
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spelling pubmed-83477412021-08-08 Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes Vaccari, Jade González-Soria, María José Carter, Nicholas Maciá, Beatriz Molecules Article A catalytic methodology for the enantioselective addition of alkylzirconium reagents to aliphatic aldehydes is reported here. The versatile and readily accessible chiral Ph-BINMOL ligand, in the presence of Ti(O(i)Pr)(4) and a zinc salt, facilitates the reaction, which proceeds under mild conditions and is compatible with functionalized nucleophiles. The alkylzirconium reagents are conveniently generated in situ by hydrozirconation of alkenes with the Schwartz reagent. This work is a continuation of our previous work on aromatic aldehydes. MDPI 2021-07-24 /pmc/articles/PMC8347741/ /pubmed/34361623 http://dx.doi.org/10.3390/molecules26154471 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Vaccari, Jade
González-Soria, María José
Carter, Nicholas
Maciá, Beatriz
Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes
title Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes
title_full Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes
title_fullStr Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes
title_full_unstemmed Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes
title_short Catalytic Enantioselective Addition of Alkylzirconium Reagents to Aliphatic Aldehydes
title_sort catalytic enantioselective addition of alkylzirconium reagents to aliphatic aldehydes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8347741/
https://www.ncbi.nlm.nih.gov/pubmed/34361623
http://dx.doi.org/10.3390/molecules26154471
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AT carternicholas catalyticenantioselectiveadditionofalkylzirconiumreagentstoaliphaticaldehydes
AT maciabeatriz catalyticenantioselectiveadditionofalkylzirconiumreagentstoaliphaticaldehydes

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