Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols

A novel biscinchona alkaloid-catalyzed highly enantioselective desymmetrization reaction of bisphenol compounds with achiral Morita–Baylis–Hillman carbonate agents was developed. Through the asymmetric allylic alkylation strategy, a broad range of optically active P-stereogenic phosphine oxides were...

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Detalles Bibliográficos
Autores principales: Yang, Guo-Hui, Li, Yao, Li, Xin, Cheng, Jin-Pei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6499109/
https://www.ncbi.nlm.nih.gov/pubmed/31105926
http://dx.doi.org/10.1039/c8sc05439h
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author Yang, Guo-Hui
Li, Yao
Li, Xin
Cheng, Jin-Pei
author_facet Yang, Guo-Hui
Li, Yao
Li, Xin
Cheng, Jin-Pei
author_sort Yang, Guo-Hui
collection PubMed
description A novel biscinchona alkaloid-catalyzed highly enantioselective desymmetrization reaction of bisphenol compounds with achiral Morita–Baylis–Hillman carbonate agents was developed. Through the asymmetric allylic alkylation strategy, a broad range of optically active P-stereogenic phosphine oxides were generated with excellent to good yields (up to 99%) and high enantioselectivities (up to 98.5 : 1.5 e.r.). The reaction was further investigated by the linear free energy relationship (LFER) analysis. A possible transition state was proposed and furthered verified by theoretical calculations.
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spelling pubmed-64991092019-05-17 Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols Yang, Guo-Hui Li, Yao Li, Xin Cheng, Jin-Pei Chem Sci Chemistry A novel biscinchona alkaloid-catalyzed highly enantioselective desymmetrization reaction of bisphenol compounds with achiral Morita–Baylis–Hillman carbonate agents was developed. Through the asymmetric allylic alkylation strategy, a broad range of optically active P-stereogenic phosphine oxides were generated with excellent to good yields (up to 99%) and high enantioselectivities (up to 98.5 : 1.5 e.r.). The reaction was further investigated by the linear free energy relationship (LFER) analysis. A possible transition state was proposed and furthered verified by theoretical calculations. Royal Society of Chemistry 2019-03-12 /pmc/articles/PMC6499109/ /pubmed/31105926 http://dx.doi.org/10.1039/c8sc05439h Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Yang, Guo-Hui
Li, Yao
Li, Xin
Cheng, Jin-Pei
Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols
title Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols
title_full Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols
title_fullStr Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols
title_full_unstemmed Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols
title_short Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols
title_sort access to p-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6499109/
https://www.ncbi.nlm.nih.gov/pubmed/31105926
http://dx.doi.org/10.1039/c8sc05439h
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