Issue 34, 2007
From the journal:

Chemical Communications

A new diastereoselective aza-allyl conjugate addition–Michael addition–ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres†

Magdaline Koutsaplis,‡a   Philip C. Andrews,*a   Steven D. Bull,b   Peter J. Duggan,c   Benjamin H. Frasera  and  Paul Jensend  

* Corresponding authors

a School of Chemistry, Monash University, Clayton, Melbourne, Australia
E-mail: phil.andrews@sci.monash.edu.au
Fax: +61 3 99054597
Tel: +61 3 99055509

b Department of Chemistry, University of Bath, Bath, UK

c CSIRO Molecular Health and Technologies, Clayton, Melbourne, Australia

d School of Chemistry, University of Sydney, Australia

Abstract

Reaction of the sodium anion of (S)-N-(α-methylbenzyl)allylamine with two equivalents of tert-butyl cinnamate results in a remarkable tandem aza-allyl conjugate addition–Michael addition–ring closure reaction, resulting in a chiral aminocyclohexane containing six new vicinal stereogenic centres with excellent levels of stereocontrol.

Graphical abstract: A new diastereoselective aza-allyl conjugate addition–Michael addition–ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres

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Article information

DOI
https://doi.org/10.1039/B707707F
Article type
Communication
Submitted
22 May 2007
Accepted
17 Jul 2007
First published
02 Aug 2007

Chem. Commun., 2007, 3580-3582

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A new diastereoselective aza-allyl conjugate addition–Michael addition–ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres

M. Koutsaplis, P. C. Andrews, S. D. Bull, P. J. Duggan, B. H. Fraser and P. Jensen, Chem. Commun., 2007, 3580 DOI: 10.1039/B707707F

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