2-Arylacetic anhydrides as ammonium enolate precursors

Louis C. Morrill; Lyndsay A. Ledingham; Jean-Philippe Couturier; Jasmine Bickel; Andrew D. Harper; Charlene Fallan; Andrew D. Smith

doi:10.1039/c3ob41869c

2-Arylacetic anhydrides as ammonium enolate precursors

Louis C. Morrill
, Lyndsay A. Ledingham
, Jean-Philippe Couturier
, Jasmine Bickel
, Andrew D. Harper
, Charlene Fallan
, Andrew D. Smith^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Readily prepared 2-arylacetic anhydrides act as convenient ammonium enolate precursors in isothiourea (HBTM-2.1)-mediated catalytic asymmetric intermolecular Michael addition-lactonisation processes, giving diverse synthetic building blocks in good yield with high diastereo- and enantiocontrol (up to 98 : 2 dr and > 99% ee).

Original language	English
Pages (from-to)	624-636
Number of pages	13
Journal	Organic & Biomolecular Chemistry
Volume	12
Issue number	4
Early online date	29 Nov 2013
DOIs	https://doi.org/10.1039/c3ob41869c
Publication status	Published - 28 Jan 2014

Keywords

Dynamic Kinetic Resolution
Tricyclic-Beta-Lactones
Acyl Transfer Catalyst
Silyl Ketene Acetals
Asymmetric Organocatalysis
Enantioselective Synthesis
Carboxylic Anhydrides
Gamma-Butyrolactones
C-Acylation
Keto Acids

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10.1039/c3ob41869c

Smith_2014_OBC_2Arylacetic_AM
© Royal Society of Chemistry 2014. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at http://dx.doi.org/10.1039/C3OB41869C
Accepted author manuscript, 1.42 MB

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RS Uni Research Fellowship Renewal 2010: University Research Fellowship - Cabranes ans Lewis Bases as Organocatalysts Synthetic Applications
Smith, A. (PI)
The Royal Society
1/10/10 → 30/09/13
Project: Fellowship

Cite this

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title = "2-Arylacetic anhydrides as ammonium enolate precursors",

abstract = "Readily prepared 2-arylacetic anhydrides act as convenient ammonium enolate precursors in isothiourea (HBTM-2.1)-mediated catalytic asymmetric intermolecular Michael addition-lactonisation processes, giving diverse synthetic building blocks in good yield with high diastereo- and enantiocontrol (up to 98 : 2 dr and > 99\% ee).",

keywords = "Dynamic Kinetic Resolution, Tricyclic-Beta-Lactones, Acyl Transfer Catalyst, Silyl Ketene Acetals, Asymmetric Organocatalysis, Enantioselective Synthesis, Carboxylic Anhydrides, Gamma-Butyrolactones, C-Acylation, Keto Acids",

author = "Morrill, \{Louis C.\} and Ledingham, \{Lyndsay A.\} and Jean-Philippe Couturier and Jasmine Bickel and Harper, \{Andrew D.\} and Charlene Fallan and Smith, \{Andrew D.\}",

note = "This work is supported by funding from the Carnegie Trust for the Universities of Scotland and EPSRC ",

year = "2014",

month = jan,

day = "28",

doi = "10.1039/c3ob41869c",

language = "English",

volume = "12",

pages = "624--636",

journal = "Organic \& Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - 2-Arylacetic anhydrides as ammonium enolate precursors

AU - Morrill, Louis C.

AU - Ledingham, Lyndsay A.

AU - Couturier, Jean-Philippe

AU - Bickel, Jasmine

AU - Harper, Andrew D.

AU - Fallan, Charlene

AU - Smith, Andrew D.

N1 - This work is supported by funding from the Carnegie Trust for the Universities of Scotland and EPSRC

PY - 2014/1/28

Y1 - 2014/1/28

N2 - Readily prepared 2-arylacetic anhydrides act as convenient ammonium enolate precursors in isothiourea (HBTM-2.1)-mediated catalytic asymmetric intermolecular Michael addition-lactonisation processes, giving diverse synthetic building blocks in good yield with high diastereo- and enantiocontrol (up to 98 : 2 dr and > 99% ee).

AB - Readily prepared 2-arylacetic anhydrides act as convenient ammonium enolate precursors in isothiourea (HBTM-2.1)-mediated catalytic asymmetric intermolecular Michael addition-lactonisation processes, giving diverse synthetic building blocks in good yield with high diastereo- and enantiocontrol (up to 98 : 2 dr and > 99% ee).

KW - Dynamic Kinetic Resolution

KW - Tricyclic-Beta-Lactones

KW - Acyl Transfer Catalyst

KW - Silyl Ketene Acetals

KW - Asymmetric Organocatalysis

KW - Enantioselective Synthesis

KW - Carboxylic Anhydrides

KW - Gamma-Butyrolactones

KW - C-Acylation

KW - Keto Acids

U2 - 10.1039/c3ob41869c

DO - 10.1039/c3ob41869c

M3 - Article

SN - 1477-0520

VL - 12

SP - 624

EP - 636

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 4

ER -

2-Arylacetic anhydrides as ammonium enolate precursors

Abstract

Keywords

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Projects

RS Uni Research Fellowship Renewal 2010: University Research Fellowship - Cabranes ans Lewis Bases as Organocatalysts Synthetic Applications

Cite this