IBX-mediated oxidative addition of isocyanides to cyclic secondary amines: total syntheses of alangiobussine and alangiobussinine. Issue 73 (21st August 2019)

• Record Type: Journal Article
• Authors: Ambule, Mayur D.; Tripathi, Shashank; Ghoshal, Anirban; Srivastava, Ajay K.
• Is Part Of: Chemical communications. Volume 55:Issue 73(2019)
• Page Start: 10872
• Page End: 10875
• Publication Date: 2019-08-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc05215a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An efficient method for synthesizing C(1)-carboxamides through IBX-mediated oxidative addition of isocyanides to cyclic secondary amines has been reported. Abstract : The present study describes a robust and general method for the synthesis of C(1)-carboxamides through IBX-mediated oxidative addition of isocyanides to tryptolines and 1, 2, 3, 4-tetrahydroisoquinolines. In this transformation, IBX plays a dual role of an oxidant and Lewis acid to activate imine facilitating isocyanide addition. Detailed mechanistic investigations were performed by isotopic labeling and real-time NMR experiments. The method was utilized for the gram scale syntheses of two alkaloids alangiobussine and alangiobussinine in 63% and 45% overall yield, respectively.