DDQ-Promoted Mild and Efficient Metal-Free Oxidative -Cyanation of N-Acyl/Sulfonyl 1,2,3,4-Tetrahydroisoquinolines

초록

A mild and highly efficient metal-free oxidative -cyanation of N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) has been accomplished at an ambient temperature via DDQ oxidation and subsequent trapping of N-acyl/sulfonyl iminium ions with (n-Bu)(3)SnCN. Employing readily removable N-acyl/sulfonyl groups as protecting groups rather than N-aryl ones enables a wide range of applications in natural product synthesis. The synthetic utility of the method was illustrated using a short and efficient formal total synthesis of (+/-)-calycotomine in three steps.

키워드