Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA.
Org Lett. 2013 Feb 1;15(3):508-11. doi: 10.1021/ol303315c. Epub 2013 Jan 23.
A highly stereoselective three-component direct Mannich reaction between aromatic aldehydes, p-toluenesulfonamide, and unfunctionalized ketones was achieved through an enolate mechanism for the first time with a bifunctional quinidine thiourea catalyst. The corresponding N-tosylated β-aminoketones were obtained in high yields and excellent diastereo- and enantioselectivities (up to >99:1 dr and >99% ee).
首次通过烯醇化物机制,使用双功能奎宁硫脲催化剂,实现了高度立体选择性的芳醛、对甲苯磺酰胺和未功能化酮之间的三组分直接曼尼希反应。相应的 N-对甲苯磺酰基-β-氨基酮以高产率和优异的非对映选择性和对映选择性(高达>99:1 dr 和>99%ee)获得。