Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent‐Based Switch in Stereopreference

The substrate scope of the asymmetric allylation with zinc organyls catalyzed by 3,3‐bis(2,4,6‐triisopropylphenyl)‐1,1‐binaphthyl‐2,2‐diyl hydrogenphosphate (TRIP) has been extended to non‐cyclic ester organozinc reagents and ketones. Tertiary chiral alcohols are obtained with ee's up to 94% an...

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Autores principales: Lazzarotto, Mattia, Hartmann, Peter, Pletz, Jakob, Belaj, Ferdinand, Kroutil, Wolfgang, Payer, Stefan E., Fuchs, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Updates
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8359974/
https://www.ncbi.nlm.nih.gov/pubmed/34413715
http://dx.doi.org/10.1002/adsc.202100037
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author Lazzarotto, Mattia
Hartmann, Peter
Pletz, Jakob
Belaj, Ferdinand
Kroutil, Wolfgang
Payer, Stefan E.
Fuchs, Michael
author_facet Lazzarotto, Mattia
Hartmann, Peter
Pletz, Jakob
Belaj, Ferdinand
Kroutil, Wolfgang
Payer, Stefan E.
Fuchs, Michael
author_sort Lazzarotto, Mattia
collection PubMed
description The substrate scope of the asymmetric allylation with zinc organyls catalyzed by 3,3‐bis(2,4,6‐triisopropylphenyl)‐1,1‐binaphthyl‐2,2‐diyl hydrogenphosphate (TRIP) has been extended to non‐cyclic ester organozinc reagents and ketones. Tertiary chiral alcohols are obtained with ee's up to 94% and two stereogenic centers can be created. Compared to the previous lactone reagent the stereopreference switches almost completely, proving the fact that the nature of the organometallic compound is of immense importance for the asymmetry of the product. [Image: see text]
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spelling pubmed-83599742021-08-17 Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent‐Based Switch in Stereopreference Lazzarotto, Mattia Hartmann, Peter Pletz, Jakob Belaj, Ferdinand Kroutil, Wolfgang Payer, Stefan E. Fuchs, Michael Adv Synth Catal Updates The substrate scope of the asymmetric allylation with zinc organyls catalyzed by 3,3‐bis(2,4,6‐triisopropylphenyl)‐1,1‐binaphthyl‐2,2‐diyl hydrogenphosphate (TRIP) has been extended to non‐cyclic ester organozinc reagents and ketones. Tertiary chiral alcohols are obtained with ee's up to 94% and two stereogenic centers can be created. Compared to the previous lactone reagent the stereopreference switches almost completely, proving the fact that the nature of the organometallic compound is of immense importance for the asymmetry of the product. [Image: see text] John Wiley and Sons Inc. 2021-05-05 2021-06-21 /pmc/articles/PMC8359974/ /pubmed/34413715 http://dx.doi.org/10.1002/adsc.202100037 Text en © 2021 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Updates
Lazzarotto, Mattia
Hartmann, Peter
Pletz, Jakob
Belaj, Ferdinand
Kroutil, Wolfgang
Payer, Stefan E.
Fuchs, Michael
Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent‐Based Switch in Stereopreference
title Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent‐Based Switch in Stereopreference
title_full Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent‐Based Switch in Stereopreference
title_fullStr Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent‐Based Switch in Stereopreference
title_full_unstemmed Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent‐Based Switch in Stereopreference
title_short Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent‐Based Switch in Stereopreference
title_sort asymmetric allylation catalyzed by chiral phosphoric acids: stereoselective synthesis of tertiary alcohols and a reagent‐based switch in stereopreference
topic Updates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8359974/
https://www.ncbi.nlm.nih.gov/pubmed/34413715
http://dx.doi.org/10.1002/adsc.202100037
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