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2-Arylacetic anhydrides as ammonium enolate precursors

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Smith_2014_OBC_2Arylacetic_AM.pdf (1.424Mb)
Date
28/01/2014
Author
Morrill, Louis C.
Ledingham, Lyndsay A.
Couturier, Jean-Philippe
Bickel, Jasmine
Harper, Andrew D.
Fallan, Charlene
Smith, Andrew D.
Funder
The Royal Society
Grant ID
UF090013
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
QD Chemistry
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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).
Citation
Morrill , L C , Ledingham , L A , Couturier , J-P , Bickel , J , Harper , A D , Fallan , C & Smith , A D 2014 , ' 2-Arylacetic anhydrides as ammonium enolate precursors ' , Organic & Biomolecular Chemistry , vol. 12 , no. 4 , pp. 624-636 . https://doi.org/10.1039/c3ob41869c
Publication
Organic & Biomolecular Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1039/c3ob41869c
ISSN
1477-0520
Type
Journal article
Rights
© 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
Description
This work is supported by funding from the Carnegie Trust for the Universities of Scotland and EPSRC
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/5916

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