Issue 51, 2012
From the journal:

Chemical Communications

Exploiting a novel size exclusion phenomenon for enantioselective acid/base cascade catalysis†

Michael E. Muratore,a   Lei Shi,‡a   Adam W. Pilling,b   R. Ian Storerc  and  Darren J. Dixon*a  

* Corresponding authors

a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK
E-mail: Darren.dixon@chem.ox.ac.uk
Fax: +44 (0)1865 285002
Tel: +44 (0)1865 275648

b School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK

c Pfizer Neusentis, The Portway Building, Granta Park, Cambridge, UK

Abstract

A novel size exclusion phenomenon between PS-BEMP and sterically bulky BPAs, has been discovered and exploited in a one-pot base-catalysed Michael addition/acid-catalysed enantioselective N-acyliminium cyclisation cascade, allowing the preparation of structurally complex β-carbolines with moderate to good enantiocontrol.

Graphical abstract: Exploiting a novel size exclusion phenomenon for enantioselective acid/base cascade catalysis

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Article information

DOI
https://doi.org/10.1039/C2CC32258G
Article type
Communication
Submitted
28 Mar 2012
Accepted
27 Apr 2012
First published
23 May 2012

Chem. Commun., 2012,48, 6351-6353

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Exploiting a novel size exclusion phenomenon for enantioselective acid/base cascade catalysis

M. E. Muratore, L. Shi<small xmlns="http://www.rsc.org/schema/rscart38"> <sup /> </small>, A. W. Pilling, R. I. Storer and D. J. Dixon, Chem. Commun., 2012, 48, 6351 DOI: 10.1039/C2CC32258G

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