Issue 91, 2012
From the journal:

Chemical Communications

Point-to-helical chirality transfer for a scalable and resolution-free synthesis of a helicenoidal DMAP organocatalyst†

Matthew R. Crittall,a   Nathan W. G. Fairhursta  and  David R. Carbery*a  

* Corresponding authors

a Department of Chemistry, University of Bath, Claverton Down, UK
E-mail: d.carbery@bath.ac.uk
Tel: +44 (0)1225 386144

Abstract

The synthesis of a second-generation [6]-helicenoidal DMAP organocatalyst is reported. The synthesis is reliant upon a highly diastereoselective Rh-catalysed [2 + 2 + 2] triyne cycloisomerization, using an existing stereocentre to control the sense of forming helicity. Taken together, a scalable (>1 g), resolution-free entry to a helical DMAP with the capacity for subsequent functionalization, has been achieved.

Graphical abstract: Point-to-helical chirality transfer for a scalable and resolution-free synthesis of a helicenoidal DMAP organocatalyst

  • This article is part of the themed collection: Chirality
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Article information

DOI
https://doi.org/10.1039/C2CC35583C
Article type
Communication
Submitted
01 Aug 2012
Accepted
23 Aug 2012
First published
24 Aug 2012

Chem. Commun., 2012,48, 11181-11183

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Point-to-helical chirality transfer for a scalable and resolution-free synthesis of a helicenoidal DMAP organocatalyst

M. R. Crittall, N. W. G. Fairhurst and D. R. Carbery, Chem. Commun., 2012, 48, 11181 DOI: 10.1039/C2CC35583C

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