Combining multi-catalysis and multi-component systems for the development of one-pot asymmetric reactions: Stereoselective synthesis of highly functionalized bicyclo[4.4.0]decane-1,6-diones

Abstract

We have developed a direct amine/acid-catalyzed stereoselective hydrogenation of a variety of Wieland-Miescher (W-M) ketones, Hajos-Parrish (H-P) ketones and their analogs with organic hydrides (Hantzsch esters) as the hydrogen source. This astonishingly simple and biomimetic approach was used to construct highly functionalized chiral bicyclo[4.4.0]decane-1,6-diones 6 in a diastereoselective fashion. This is an example of the development of a new technology by the combination of multiple catalysts and components in one pot to deliver highly functionalized chiral molecules. © The Royal Society of Chemistry 2008.