Secondary-secondary diamine catalysts for the enantioselective Michael addition of cyclic ketones to nitroalkenes

作者：Pansare Sunil V^*; Kirby Raie Lene

来源：Tetrahedron, 2009, 65(23): 4557-4561.

DOI：10.1016/j.tet.2009.03.093

Secondary-secondary diamines derived from S-proline are efficient catalysts for the ketone-nitroalkene Michael addition reaction. The stereoselectivity of the Michael addition is dependant on the pK(a) of the N-substituted aminomethyl pendant in these diamines. N'-Aryl aminomethyl pyrrolidines provide gamma-nitroketones with moderate to good enantiomeric excess (65-92%). Removal of the hydrogen-bond donor group by N-methylation results in a dramatic reduction of enantioselectivity (average ee 6%).

• 出版日期2009-6-6