Issue 12, 2012
From the journal:

Chemical Communications

Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents†

Pieter H. Bos,a   Alena Rudolph,a   Manuel Pérez,a   Martín Fañanás-Mastral,a   Syuzanna R. Harutyunyana  and  Ben L. Feringa*a  

* Corresponding authors

a Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, Groningen, The Netherlands
E-mail: b.l.feringa@rug.nl
Fax: +31 50 363 4296
Tel: +31 50 363 4235

Abstract

A highly efficient method is reported for the asymmetric ring opening of oxabicyclic alkenes with organolithium reagents. Using a copper/chiral phosphoramidite complex together with a Lewis acid (BF3·OEt2), full selectivity for the anti isomer and excellent enantioselectivities were obtained for the ring opened products.

Graphical abstract: Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents

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Article information

DOI
https://doi.org/10.1039/C2CC16855C
Article type
Communication
Submitted
04 Nov 2011
Accepted
08 Dec 2011
First published
03 Jan 2012

Chem. Commun., 2012,48, 1748-1750

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Copper-catalyzed asymmetric ring opening of oxabicyclic alkenes with organolithium reagents

P. H. Bos, A. Rudolph, M. Pérez, M. Fañanás-Mastral, S. R. Harutyunyan and B. L. Feringa, Chem. Commun., 2012, 48, 1748 DOI: 10.1039/C2CC16855C

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