Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins
Date
18/07/2022Author
Grant ID
EP/T023643/1
EP/S019359
EP/L016419/1
EP/T023643/1
EP/S019359
Metadata
Show full item recordAltmetrics Handle Statistics
Altmetrics DOI Statistics
Abstract
Enantioselective [2+2] cycloaddition of C(1)-ammonium enolates generated catalytically using the isothiourea HyperBTM with N alkyl isatins gives spirocyclic β-lactones. In situ ring-opening with an amine nucleophile generates isolable highly enantioenriched products in up to 92:8 dr and in >99:1 er.
Citation
Abdelhamid , Y , Kasten , K , Dunne , J , Hartley , W , Young , C M , Cordes , D B , Slawin , A M Z , Ng , S & Smith , A D 2022 , ' Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins ' , Organic Letters , vol. Articles ASAP . https://doi.org/10.1021/acs.orglett.2c02170
Publication
Organic Letters
Status
Peer reviewed
ISSN
1523-7060Type
Journal article
Rights
Copyright © 2022 The Authors. Published by American Chemical Society.This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Description
The research leading to these results has received funding from the EPSRC (EP/S019359/1, C. Y.; EP/T023643/1, J. D.; K. K.) as well as Syngenta and the EPSRC Centre for Doctoral Training in Critical Resource Catalysis [CRITICAT, EP/L016419/1 (W.C.H.)].Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.
Related items
Showing items related by title, author, creator and subject.
-
Constitutionally selective dynamic covalent nanoparticle assembly
Marro, Nicolas; Suo, Rongtian; Naden, Aaron B.; Kay, Euan R. (2022-07-28) - Journal articleThe future of materials chemistry will be defined by our ability to precisely arrange components that have considerably larger dimensions and more complex compositions than conventional molecular or macromolecular building ... -
High-resolution solid-state 13C NMR spectroscopy of the paramagnetic metal-organic frameworks, STAM-1 and HKUST-1
Dawson, Daniel M.; Jamieson, Lauren E.; Mohideen, M. Infas H.; McKinlay, Alistair C.; Smellie, Iain A.; Cadou, Romain; Keddie, Neil S.; Morris, Russell E.; Ashbrook, Sharon E. (2012-11) - Journal articleSolid-state C-13 magic-angle spinning (MAS) NMR spectroscopy is used to investigate the structure of the Cu(II)-based metal-organic frameworks (MOFs), HKUST-1 and STAM-1, and the structural changes occurring within these ... -
Calculating NMR parameters in aluminophosphates : evaluation of dispersion correction schemes
Sneddon, Scott; Dawson, Daniel M.; Pickard, Chris J.; Ashbrook, Sharon E. (2014-02) - Journal articlePeriodic density functional theory (DFT) calculations have recently emerged as a popular tool for assigning solid-state nuclear magnetic resonance (NMR) spectra. However, in order for the calculations to yield accurate ...