Kinetic resolution of racemic tertiary allylic alcohols through SN2′ 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...

Full description

Saved in:
Bibliographic Details
Published in:Chemical science (Cambridge) 2022-08, Vol.13 (33), p.9607-9613
Main Authors: Kayal, Satavisha, Kikuchi, Jun, Shinagawa, Naoya, Umemiya, Shigenobu, Terada, Masahiro
Format: Article
Language:English
Subjects:
Alcohols
Catalysts
Chemistry
Enantiomers
Substitution reactions
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/d2sc03052g