St Andrews Research Repository

St Andrews University Home
View Item 
  •   St Andrews Research Repository
  • University of St Andrews Research
  • University of St Andrews Research
  • University of St Andrews Research
  • View Item
  •   St Andrews Research Repository
  • University of St Andrews Research
  • University of St Andrews Research
  • University of St Andrews Research
  • View Item
  •   St Andrews Research Repository
  • University of St Andrews Research
  • University of St Andrews Research
  • University of St Andrews Research
  • View Item
  • Login
JavaScript is disabled for your browser. Some features of this site may not work without it.

Isothiourea-catalyzed [2+2] cycloaddition of C(1)-ammonium enolates and N-alkyl isatins

Thumbnail
View/Open
Abdelhamid_2022_OL_Isothiourea_CC.pdf (1.558Mb)
Date
18/07/2022
Author
Abdelhamid, Yusra
Kasten, Kevin
Dunne, Joanne
Hartley, Will
Young, Claire M.
Cordes, David B.
Slawin, Alexandra M. Z.
Ng, Sean
Smith, Andrew D.
Funder
EPSRC
EPSRC
EPSRC
EPSRC
EPSRC
Grant ID
EP/T023643/1
EP/S019359
EP/L016419/1
EP/T023643/1
EP/S019359
Keywords
QD Chemistry
DAS
Metadata
Show full item record
Altmetrics 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
DOI
https://doi.org/10.1021/acs.orglett.2c02170
ISSN
1523-7060
Type
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
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/25678

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 article
    The 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 article
    Solid-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 article
    Periodic 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 ...
Advanced Search

Browse

All of RepositoryCommunities & CollectionsBy Issue DateNamesTitlesSubjectsClassificationTypeFunderThis CollectionBy Issue DateNamesTitlesSubjectsClassificationTypeFunder

My Account

Login

Open Access

To find out how you can benefit from open access to research, see our library web pages and Open Access blog. For open access help contact: openaccess@st-andrews.ac.uk.

Accessibility

Read our Accessibility statement.

How to submit research papers

The full text of research papers can be submitted to the repository via Pure, the University's research information system. For help see our guide: How to deposit in Pure.

Electronic thesis deposit

Help with deposit.

Repository help

For repository help contact: Digital-Repository@st-andrews.ac.uk.

Give Feedback

Cookie policy

This site may use cookies. Please see Terms and Conditions.

Usage statistics

COUNTER-compliant statistics on downloads from the repository are available from the IRUS-UK Service. Contact us for information.

© University of St Andrews Library

University of St Andrews is a charity registered in Scotland, No SC013532.

  • Facebook
  • Twitter