UMR CNRS 6263 iSm2, Aix-Marseille Université, Centre Saint Jérôme, service 531, 13397 Marseille, France.
Org Lett. 2010 Nov 19;12(22):5246-9. doi: 10.1021/ol102289g. Epub 2010 Oct 25.
The first organocatalytic enantio- and diastereoselective conjugate addition of α-ketoamides to nitroalkenes has been achieved using a bifunctional amino thiourea catalyst. In this new approach, the substrate amide proton plays a critical role in the formation of the Michael anti-adducts in high yields and high stereoselectivities. To illustrate the high synthetic potential of this methodology, the diastereo- and enantioselective synthesis of a hexasubstituted cyclohexane via a Michael-Michael-Henry cascade reaction is described.
首次实现了使用双功能氨基硫脲催化剂，对α-酮酰胺与硝基烯烃的对映选择性和非对映选择性共轭加成反应。在这种新方法中，底物酰胺质子在形成迈克尔反加物方面发挥了关键作用，从而以高产率和高立体选择性得到产物。为了说明该方法的高合成潜力，通过迈克尔-迈克尔-亨利级联反应，描述了六取代环己烷的非对映选择性和对映选择性合成。
