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.

Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis

Thumbnail
View/Open
Smith_et_al_2015_Chemistry_An_Asian_Journal_CC.pdf (601.1Kb)
Date
04/02/2016
Author
Stark, Daniel Graham
Morrill, Louis Christian
Cordes, David Bradford
Slawin, Alexandra Martha Zoya
O'Riordan, Timothy J.C.
Smith, Andrew David
Keywords
QD Chemistry
DAS
Metadata
Show full item record
Abstract
The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalysed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonisation/lactamisation cascade. Notably, in order to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90% ee). The derivatisation of the heterocyclic core of a model 3,5,6-substituted dihydropyranone through hydrogenation is also reported.
Citation
Stark , D G , Morrill , L C , Cordes , D B , Slawin , A M Z , O'Riordan , T J C & Smith , A D 2016 , ' Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis ' , Chemistry-An Asian Journal , vol. 11 , no. 3 , pp. 395–400 . https://doi.org/10.1002/asia.201500907
Publication
Chemistry-An Asian Journal
Status
Peer reviewed
DOI
https://doi.org/10.1002/asia.201500907
ISSN
1861-4728
Type
Journal article
Rights
Copyright 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Description
We thank the Royal Society for a University Research Fellowship (ADS), Syngenta and EPSRC grant No. EP/K503162/1 (DGS), and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850, for funding.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/7792

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