Aryloxide-promoted catalyst turnover in Lewis base organocatalysis

Will C. Hartley; Timothy J. C. O'Riordan; Andrew D. Smith

doi:10.1055/s-0036-1589047

Aryloxide-promoted catalyst turnover in Lewis base organocatalysis

Will C. Hartley, Timothy J. C. O'Riordan, Andrew D. Smith

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

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

Original language	English
Pages (from-to)	3303-3310
Journal	Synthesis
Volume	49
Issue number	15
Early online date	26 Jun 2017
DOIs	https://doi.org/10.1055/s-0036-1589047
Publication status	Published - Aug 2017

Keywords

Lewis base catalysis
catalyst turnover and release
Aryloxide
Isothiourea
NHC
Tertiary amines

Access to Document

10.1055/s-0036-1589047

Smith_2017_Synthesis_Aryloxide_AAM
© 2017 Georg Thieme Verlag Stuttgart · New York. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1055/s-0036-1589047
Accepted author manuscript, 1.99 MB

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
CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. D. (PI), Nolan, S. P. (CoI) & Westwood, N. J. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard
ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis
Smith, A. D. (PI)
European Commission
1/10/11 → 30/06/17
Project: Standard

Cite this

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title = "Aryloxide-promoted catalyst turnover in Lewis base organocatalysis",

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",

keywords = "Lewis base catalysis, catalyst turnover and release, Aryloxide, Isothiourea, NHC, Tertiary amines",

author = "Hartley, {Will C.} and O'Riordan, {Timothy J. C.} and Smith, {Andrew D.}",

note = "The authors thank Syngenta and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1) (WCH) for funding. The European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged (ADS). ADS thanks the Royal Society for a Wolfson Research Merit Award.",

year = "2017",

month = aug,

doi = "10.1055/s-0036-1589047",

language = "English",

volume = "49",

pages = "3303--3310",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Aryloxide-promoted catalyst turnover in Lewis base organocatalysis

AU - Hartley, Will C.

AU - O'Riordan, Timothy J. C.

AU - Smith, Andrew D.

N1 - The authors thank Syngenta and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1) (WCH) for funding. The European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged (ADS). ADS thanks the Royal Society for a Wolfson Research Merit Award.

PY - 2017/8

Y1 - 2017/8

N2 - 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

AB - 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

KW - Lewis base catalysis

KW - catalyst turnover and release

KW - Aryloxide

KW - Isothiourea

KW - NHC

KW - Tertiary amines

U2 - 10.1055/s-0036-1589047

DO - 10.1055/s-0036-1589047

M3 - Review article

SN - 0039-7881

VL - 49

SP - 3303

EP - 3310

JO - Synthesis

JF - Synthesis

IS - 15

ER -

Aryloxide-promoted catalyst turnover in Lewis base organocatalysis

Abstract

Keywords

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Projects

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

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

ERC Starting Grant EnolCat: Emulating nature: Reaction diversity and understanding through asymmetric catalysis

Cite this