Issue 2, 2015
From the journal:

Chemical Science

Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions†

Alejandro Cabanillas,a   Christopher D. Davies,b   Louise Malea  and  Nigel S. Simpkins*a  

* Corresponding authors

a School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT UK

b AstraZeneca, Innovative Medicines, Alderley Park, SK10 4TG UK

Abstract

Michael addition reactions of triketopiperazine (TKP) derivatives to enones, mediated by a cinchona alkaloid-derived catalyst, deliver products in high yield and enantiomeric ratio (er). Use of unsaturated ester, nitrile or sulfone partners gives bridged hydroxy-diketopiperazine (DKP) products resulting from a novel Michael addition–ring closure.

Graphical abstract: Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

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Article information

DOI
https://doi.org/10.1039/C4SC03218G
Article type
Edge Article
Submitted
20 Oct 2014
Accepted
26 Nov 2014
First published
28 Nov 2014
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., 2015,6, 1350-1354

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Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

A. Cabanillas, C. D. Davies, L. Male and N. S. Simpkins, Chem. Sci., 2015, 6, 1350 DOI: 10.1039/C4SC03218G

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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