Kinetic resolution of racemic tertiary allylic alcohols through S(N)2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system

A highly efficient kinetic resolution (KR) of racemic tertiary allylic alcohols was achieved through an intramolecular allylic substitution reaction using a co-catalyst system composed of chiral bisphosphoric acid and silver carbonate. This reaction afforded enantioenriched diene monoepoxides along...

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Autores principales: Kayal, Satavisha, Kikuchi, Jun, Shinagawa, Naoya, Umemiya, Shigenobu, Terada, Masahiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400685/
https://www.ncbi.nlm.nih.gov/pubmed/36091917
http://dx.doi.org/10.1039/d2sc03052g
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author Kayal, Satavisha
Kikuchi, Jun
Shinagawa, Naoya
Umemiya, Shigenobu
Terada, Masahiro
author_facet Kayal, Satavisha
Kikuchi, Jun
Shinagawa, Naoya
Umemiya, Shigenobu
Terada, Masahiro
author_sort Kayal, Satavisha
collection PubMed
description A highly efficient kinetic resolution (KR) of racemic tertiary allylic alcohols was achieved through an intramolecular allylic substitution reaction using a co-catalyst system composed of chiral bisphosphoric acid and silver carbonate. This reaction afforded enantioenriched diene monoepoxides along with the recovery of tertiary allylic alcohols in a highly enantioselective manner, realizing an extremely high s-factor in most cases. The present method provides a new access to enantioenriched tertiary allylic alcohols, multifunctional compounds that are applicable for further synthetic manipulations.
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spelling pubmed-94006852022-09-08 Kinetic resolution of racemic tertiary allylic alcohols through S(N)2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system Kayal, Satavisha Kikuchi, Jun Shinagawa, Naoya Umemiya, Shigenobu Terada, Masahiro Chem Sci Chemistry A highly efficient kinetic resolution (KR) of racemic tertiary allylic alcohols was achieved through an intramolecular allylic substitution reaction using a co-catalyst system composed of chiral bisphosphoric acid and silver carbonate. This reaction afforded enantioenriched diene monoepoxides along with the recovery of tertiary allylic alcohols in a highly enantioselective manner, realizing an extremely high s-factor in most cases. The present method provides a new access to enantioenriched tertiary allylic alcohols, multifunctional compounds that are applicable for further synthetic manipulations. The Royal Society of Chemistry 2022-07-20 /pmc/articles/PMC9400685/ /pubmed/36091917 http://dx.doi.org/10.1039/d2sc03052g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Kayal, Satavisha
Kikuchi, Jun
Shinagawa, Naoya
Umemiya, Shigenobu
Terada, Masahiro
Kinetic resolution of racemic tertiary allylic alcohols through S(N)2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system
title Kinetic resolution of racemic tertiary allylic alcohols through S(N)2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system
title_full Kinetic resolution of racemic tertiary allylic alcohols through S(N)2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system
title_fullStr Kinetic resolution of racemic tertiary allylic alcohols through S(N)2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system
title_full_unstemmed Kinetic resolution of racemic tertiary allylic alcohols through S(N)2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system
title_short Kinetic resolution of racemic tertiary allylic alcohols through S(N)2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system
title_sort kinetic resolution of racemic tertiary allylic alcohols through s(n)2′ reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400685/
https://www.ncbi.nlm.nih.gov/pubmed/36091917
http://dx.doi.org/10.1039/d2sc03052g
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