Back to Search Start Over

Domino Michael-aldol annulations for the stereocontrolled synthesis of bicyclo[3.3.1]nonane and bicyclo[3.2.1]octane derivatives

Authors :
Charles M. Marson
Jean-Alexandre Richard
Rossella Promontorio
Source :
RSC Advances. 6:114412-114424
Publication Year :
2016
Publisher :
Royal Society of Chemistry (RSC), 2016.

Abstract

Domino Michael-aldol annulation of cycloalkane-1,3-diones with enals affords a general route to 6-hydroxybicyclo[3.3.1]nonane-2,9-diones and 2-hydroxybicyclo[3.2.1]octane-6,8-diones, notably in one-pot procedures under convenient conditions. The annulation is shown to be compatible with one or more substituents at six positions of the bicyclo[3.3.1]nonane-2,9-dione scaffold. In some cases, the relative configuration of the product can be controlled by the appropriate choice of solvent, base and temperature for the annulation. In contrast to the chair–chair conformations usually adopted, the bicyclo compounds derived from 2,4,4-trimethylcyclohexane-1,3-dione possessed boat-chair conformations. Oxidation of the annulation products gave the corresponding bicyclo triketones.

Details

ISSN :
20462069
Volume :
6
Database :
OpenAIRE
Journal :
RSC Advances
Accession number :
edsair.doi...........340b396c2ef912354402e605ff1d1d8f
Full Text :
https://doi.org/10.1039/c6ra23523a