Total Synthesis of Pyrrolidine and Piperidine Natural Products Via TMSOTf-Mediated "5/6-Endo-dig" Reductive Hydroamination of Enynyl Amines.
Organic Letters(2023)
Abstract
Stereoselective syntheses of pyrrolidines and piperidines bearing hydrophobic chains have been achieved through a metal free, Lewis acid-mediated 5/6-endo-dig reductive hydroamination cascade of enynyl amines. The brevity of the developed strategy allowed for the collective stereoselective total synthesis of various alkaloids, including (±)-pyrrolidine cis-225H, (±)-epi-197B, (±)-epi-225C, the family of (+)-solenopsins and (+)-isosolenopsins, and the formal synthesis of (±)-bgugaine and (+)-azimic acid.
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Key words
Pyridine Derivatives,Total Synthesis,Enantioselective Synthesis,Alkaloids
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