Issue 12, 2009

Asymmetric synthesis of 2-azabicyclo[3.3.1]nonanes by a microwave-assisted organocatalysed tandem desymmetrisation and intramolecular aldolisation

Abstract

The six-membered nitrogen-containing ring of the morphan scaffold, ubiquitous in natural products, is formed by an intramolecular aldol process of an aza-tethered dicarbonyl compound, leading to the first asymmetric synthesis of a morphan derivative using organocatalysis.

Graphical abstract: Asymmetric synthesis of 2-azabicyclo[3.3.1]nonanes by a microwave-assisted organocatalysed tandem desymmetrisation and intramolecular aldolisation

Supplementary files

Article information

Article type
Communication
Submitted
06 Apr 2009
Accepted
06 May 2009
First published
18 May 2009

Org. Biomol. Chem., 2009,7, 2517-2519

Asymmetric synthesis of 2-azabicyclo[3.3.1]nonanes by a microwave-assisted organocatalysed tandem desymmetrisation and intramolecular aldolisation

F. Diaba and J. Bonjoch, Org. Biomol. Chem., 2009, 7, 2517 DOI: 10.1039/B906835J

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