Generation and reactivity of C(1)-ammonium enolates using isothiourea catalysis

Calum McLaughlin; Andrew D. Smith

doi:10.1002/chem.202002059

Generation and reactivity of C(1)-ammonium enolates using isothiourea catalysis

Research output: Contribution to journal › Review article › peer-review

Abstract

C(1)-ammonium enolates are powerful, catalytically generated synthetic intermediates applied in the enantioselective α-functionalization of carboxylic acid derivatives. This review describes the recent developments in the generation and application of C(1)-ammonium enolates from various precursors (carboxylic acids, anhydrides, acyl imidazoles, aryl esters, α-diazoketones, alkyl halides) using isothiourea Lewis base organocatalysts. Their synthetic utility in intra- and intermolecular enantioselective C-C and C-X bond forming processes on reaction with various electrophiles will be showcased utilizing two distinct catalyst turnover approaches.

Original language	English
Journal	Chemistry - A European Journal
Volume	Early View
Early online date	10 Nov 2020
DOIs	https://doi.org/10.1002/chem.202002059
Publication status	E-pub ahead of print - 10 Nov 2020

Keywords

Aryloxides
C(1)-ammonium enolates
Catalyst turnover
Formal cycloaddition
Isothioureas

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10.1002/chem.202002059Licence: CC BY

McLaughlin_2020_CEJ_C(1)_CC
Copyright © 2020 The Authors. Published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 7.72 MBLicence: CC BY

RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications
Smith, A. D. (PI)
The Royal Society
1/01/15 → 31/12/19
Project: Fellowship

Cite this

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title = "Generation and reactivity of C(1)-ammonium enolates using isothiourea catalysis",

abstract = "C(1)-ammonium enolates are powerful, catalytically generated synthetic intermediates applied in the enantioselective α-functionalization of carboxylic acid derivatives. This review describes the recent developments in the generation and application of C(1)-ammonium enolates from various precursors (carboxylic acids, anhydrides, acyl imidazoles, aryl esters, α-diazoketones, alkyl halides) using isothiourea Lewis base organocatalysts. Their synthetic utility in intra- and intermolecular enantioselective C-C and C-X bond forming processes on reaction with various electrophiles will be showcased utilizing two distinct catalyst turnover approaches.",

keywords = "Aryloxides, C(1)-ammonium enolates, Catalyst turnover, Formal cycloaddition, Isothioureas",

author = "Calum McLaughlin and Smith, {Andrew D.}",

note = "Funding: UK EPSRC (EP/M508214/1, C.M.). Royal Society for a Wolfson Research Merit Award (A.D.S.).",

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doi = "10.1002/chem.202002059",

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volume = "Early View",

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T1 - Generation and reactivity of C(1)-ammonium enolates using isothiourea catalysis

AU - McLaughlin, Calum

AU - Smith, Andrew D.

N1 - Funding: UK EPSRC (EP/M508214/1, C.M.). Royal Society for a Wolfson Research Merit Award (A.D.S.).

PY - 2020/11/10

Y1 - 2020/11/10

N2 - C(1)-ammonium enolates are powerful, catalytically generated synthetic intermediates applied in the enantioselective α-functionalization of carboxylic acid derivatives. This review describes the recent developments in the generation and application of C(1)-ammonium enolates from various precursors (carboxylic acids, anhydrides, acyl imidazoles, aryl esters, α-diazoketones, alkyl halides) using isothiourea Lewis base organocatalysts. Their synthetic utility in intra- and intermolecular enantioselective C-C and C-X bond forming processes on reaction with various electrophiles will be showcased utilizing two distinct catalyst turnover approaches.

AB - C(1)-ammonium enolates are powerful, catalytically generated synthetic intermediates applied in the enantioselective α-functionalization of carboxylic acid derivatives. This review describes the recent developments in the generation and application of C(1)-ammonium enolates from various precursors (carboxylic acids, anhydrides, acyl imidazoles, aryl esters, α-diazoketones, alkyl halides) using isothiourea Lewis base organocatalysts. Their synthetic utility in intra- and intermolecular enantioselective C-C and C-X bond forming processes on reaction with various electrophiles will be showcased utilizing two distinct catalyst turnover approaches.

KW - Aryloxides

KW - C(1)-ammonium enolates

KW - Catalyst turnover

KW - Formal cycloaddition

KW - Isothioureas

U2 - 10.1002/chem.202002059

DO - 10.1002/chem.202002059

M3 - Review article

SN - 0947-6539

VL - Early View

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

ER -

Generation and reactivity of C(1)-ammonium enolates using isothiourea catalysis

Abstract

Keywords

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Projects

RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications

Cite this