64275-74-7Relevant academic research and scientific papers
Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products
Dion, Isabelle,Vincent-Rocan, Jean-Francois,Zhang, Lei,Cebrowski, Pamela H.,Lebrun, Marie-Eve,Pfeiffer, Jennifer Y.,Bedard, Anne-Catherine,Beauchemin, Andre M.
, p. 12735 - 12749 (2014/01/17)
Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.
