Issue 5, 2013
From the journal:

Chemical Science

Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes†

Emily R. T. Robinson,a   Charlene Fallan,a   Carmen Simal,a   Alexandra M. Z. Slawina  and  Andrew D. Smith*a  

* Corresponding authors

a EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, UK
E-mail: ads10@st-andrews.ac.uk

Abstract

The asymmetric annulation of a range of α,β-unsaturated acyl ammonium intermediates, formed from isothiourea HBTM 2.1 and anhydrides with either 1,3-dicarbonyls, β-ketoesters or azaaryl ketones gives either functionalised esters (upon ring opening), dihydropyranones or dihydropyridones in good yields (up to 93%) and high enantioselectivity (up to 97% ee).

Graphical abstract: Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

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Article information

DOI
https://doi.org/10.1039/C3SC50199J
Article type
Edge Article
Submitted
22 Jan 2013
Accepted
01 Mar 2013
First published
01 Mar 2013
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2013,4, 2193-2200

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Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

E. R. T. Robinson, C. Fallan, C. Simal, A. M. Z. Slawin and A. D. Smith, Chem. Sci., 2013, 4, 2193 DOI: 10.1039/C3SC50199J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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