Synthesis Workshop Videos - 2020-10-31
In this Research Spotlight episode, Dr. Alberto Vega-Peñaloza joins us to explain his work on visible-light [2+2] heterocycloadditions. Parent references: Chem. Sci., 2020, 11, 6532-6538 Eur. J. Org. Chem. 2020, DOI:10.1002/ejoc.202001057 Other references (in order of appearance): W. Gribble, Indole Ring Synthesis: From Natural Products to Drug Discovery, 1st edn, Wiley-VCH, Weinheim, 2016 J. A. Burkhard et al. Angew. Chem. Int. Ed. 2010, 49, 9052 – 9067 a) E. Paternò, G. Chieffi, Gazz. Chim. Ital. 1909, 39, 341–361; b) G. Büchi, C. G. Inman, E. S. Lipinsky, J. Am. Chem. Soc. 1954, 76, 4327–4331 a) D. Cheng, Y. Ishihara, B. Tan, C. F. Barbas III, ACS Catal. 2014, 4, 743–762; b) J. Bariwal, L. G. Voskressensky, E. V. Van der Eycken, Chem. Soc. Rev. 2018, 47, 3831; c) K. Liang, N. Li, Y. Zhang, T. Li, C. Xia, Chem. Sci. 2019, 10, 3049–3053
Samuel Mun - 2020-10-31
it's pretty interesting that the lower energy n orbital centered on the oxygen attacks first rather than the higher energy pi* orbital centered on the carbonyl carbon. I mean i guess it's not that interesting because this is an established transformation. but still interesting from a "fresh out of undergrad" perspective.