Issue 46, 2013
From the journal:

Chemical Communications

Enantio- and diastereoselective palladium catalysed arylative and vinylative allene carbocyclisation cascades†

Meiling Li,a   Alison Hawkins,a   David M. Barber,a   Patrick Bultinck,b   Wouter Herreboutc  and  Darren J. Dixon*a  

* Corresponding authors

a Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK
E-mail: darren.dixon@chem.ox.ac.uk

b Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281-S3, 9000 Gent, Belgium

c Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium

Abstract

The enantioselective synthesis of heavily decorated spirolactams has been accomplished via an arylative or vinylative allene carbocyclisation cascade. Mediated by silver phosphate, a range of allene-linked pro-nucleophiles and aryl or vinyl iodides were reacted in the presence of catalytic Pd(OAc)2 and chiral bis(oxazoline) ligands to afford the spirolactam products in good yields and high enantio- and diastereoselectivities.

Graphical abstract: Enantio- and diastereoselective palladium catalysed arylative and vinylative allene carbocyclisation cascades

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Article information

DOI
https://doi.org/10.1039/C3CC42079E
Article type
Communication
Submitted
21 Mar 2013
Accepted
19 Apr 2013
First published
19 Apr 2013

Chem. Commun., 2013,49, 5265-5267

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Enantio- and diastereoselective palladium catalysed arylative and vinylative allene carbocyclisation cascades

M. Li, A. Hawkins, D. M. Barber, P. Bultinck, W. Herrebout and D. J. Dixon, Chem. Commun., 2013, 49, 5265 DOI: 10.1039/C3CC42079E

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