Aryloxide-Promoted Catalyst Turnover in Lewis Base Organo­catalysis

Dedicated to Prof. Herbert Mayr on the occasion of his 70^th birthday.

Abstract

This short review highlights select examples of enantioselective Lewis base promoted reactions that use tertiary amine (cinchona alkaloids, isothioureas, and DMAP/PPY derivatives) or NHC catalysts and employ aryloxide-promoted catalyst turnover from an acyl ammonium or azolium intermediate. This review focuses on the range of strategies that have been developed within this area, and discusses their evolution and context.

1 Introduction

2 Phenols as Additives To Promote Catalyst Turnover

2.1 NHC Catalysis with α-Functionalised Aldehydes and Phenols

2.2 Enantioselective Fluorination with Aryloxide-Promoted Catalyst Turnover

3 In Situ Catalytic Generation Of Aryloxide

3.1 Aryloxide-Promoted Turnover Generated from an Electrophilic Polyhalogenated Quinone: Overview

3.2 Aryloxide-Promoted Catalyst Turnover Generated from an α-Aryl­oxyaldehyde or Aryl Ester Starting Material: Overview

4 Summary and Outlook

Key words

Lewis base catalysis - catalyst turnover and release - aryl­oxide - isothiourea - NHC - tertiary amines

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