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
  • Register / Login
JavaScript is disabled for your browser. Some features of this site may not work without it.

Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters

Thumbnail
View/Open
Shu_2019_CS_Michael_CC.pdf (1.107Mb)
Date
23/10/2019
Author
Shu, Chang
Liu, Honglei
Slawin, Alexandra
Carpenter-Warren, Cameron L.
Smith, Andrew David
Funder
The Royal Society
The Royal Society
Grant ID
NF170330
WM140071
Keywords
QD Chemistry
DAS
Metadata
Show full item record
Abstract
The isothiourea-catalysed enantioselective Michael addition of 3-aryloxindole and 4-substituted-dihydropyrazol-3-one pronucleophiles to α,β-unsaturated p-nitrophenyl esters is reported. This process generates products containing two contiguous stereocentres, one quaternary, in good yields and excellent enantioselectivities (>30 examples, up to > 95 : 5 dr and 99 : 1 er). This protocol harnesses the multifunctional ability of p-nitrophenoxide to promote effective catalysis. In contrast to previous methodologies using tertiary amine Lewis bases, in which the pronucleophile was used as the solvent, this work allows bespoke pronucleophiles to be used in stoichiometric quantities.
Citation
Shu , C , Liu , H , Slawin , A , Carpenter-Warren , C L & Smith , A D 2019 , ' Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters ' , Chemical Science , vol. Advance Article . https://doi.org/10.1039/C9SC04303A
Publication
Chemical Science
Status
Peer reviewed
DOI
https://doi.org/10.1039/C9SC04303A
ISSN
2041-6520
Type
Journal article
Rights
Copyright © 2019 The Author(s). Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Description
The research leading to these results (C. S., H. L.) has received funding from the Royal Society Newton Fellowship Programme. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/18937

Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.

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