Synthesis of Cyclic Peptidomimetics via a Pd-Catalyzed Macroamination Reaction

• DOI: 10.1021/acs.orglett.6b01961
• Publication Date: 2016-08-10T16:39:23Z
• Authors: Brett A. Hopkins; Graham F. Smith; Nunzio Sciammetta
• Keywords: 01 natural sciences; 0104 chemical sciences

A new method to access cyclic peptidomimetics via a Pd-catalyzed macroamination reaction is presented. Natural amino acid amines are revealed as proficient coupling partners in these transformations. With a commercially available CPhos G3 catalyst system and substrates bearing diverse amino acid and aryl halide backbones, the unique head to side-chain (or side-chain mimic) macrocycles are afforded with ring sizes from 11 to 23 members in yields up to 84%.