Issue 55, 2013

First asymmetric synthesis of planar chiral [2.2]metacyclophanes

Abstract

A general three step asymmetric synthesis of planar chiral [2.2]metacyclophanes utilizing selective benzylic and aryl metalations is described. The final enantioselective step is achieved using a (−)-sparteine mediated aryl metalation, following which electrophile reaction gives planar chiral cyclophanes with enantiomeric ratios (er) above 90 : 10.

Graphical abstract: First asymmetric synthesis of planar chiral [2.2]metacyclophanes

Supplementary files

Article information

Article type
Communication
Submitted
28 Mar 2013
Accepted
14 Apr 2013
First published
17 Apr 2013

Chem. Commun., 2013,49, 6125-6127

First asymmetric synthesis of planar chiral [2.2]metacyclophanes

M. Blangetti, H. Müller-Bunz and D. F. O'Shea, Chem. Commun., 2013, 49, 6125 DOI: 10.1039/C3CC42275E

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