Organocatalytic Mitsunobu Reactions скачать в хорошем качестве

Organocatalytic Mitsunobu Reactions

In this episode we analyze a new paper from the Denton lab where they report a redox-neutral organocatalytic Mitsunobu reaction eliminating the need for stoichiometric, hazardous reagents. DOI: 10.1126/science.aax3353 References: Beddoe, R. H.; Andrews, K. G.; Magné, V.; Cuthbertson, J. D.; Saska, J.; Shannon-Little, A. L.; Shanahan, S. E.; Sneddon, H. F.; Denton, R. M. Redox-Neutral Organocatalytic Mitsunobu Reactions. Science 2019, 365, 910–914. An, J.; Denton, R. M.; Lambert, T. H.; Nacsa, E. D. The Development of Catalytic Nucleophilic Substitution Reactions: Challenges, Progress and Future Directions. Org. Biomol. Chem. 2014, 12, 2993-3003. Mitsunobu, O.; Yamada, M. Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts . Bull. Chem. Soc. Jpn. 1967, 40, 2380–2382. Mitsunobu, O. The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products. Synthesis 1981, 1981, 1–28. Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Mitsunobu and Related Reactions: Advances and Applications. Chem. Rev. 2009, 109, 2551–2651. But, T. Y. S.; Toy, P. H. Organocatalytic Mitsunobu Reactions. J. Am. Chem. Soc. 2006, 128, 9636–9637. Hirose, D.; Taniguchi, T.; Ishibashi, H. Recyclable Mitsunobu Reagents: Catalytic Mitsunobu Reactions with an Iron Catalyst and Atmospheric Oxygen. Angew. Chemie Int. Ed. 2013, 52, 4613-4617. Buonomo, J. A.; Aldrich, C. C. Mitsunobu Reactions Catalytic in Phosphine and a Fully Catalytic System. Angew. Chemie Int. Ed. 2015, 127, 13233–13236. Hirose, D.; Gazvoda, M.; Košmrlj, J.; Taniguchi, T. The “Fully Catalytic System” in Mitsunobu Reaction Has Not Been Realized Yet. Org. Lett. 2016, 18, 4036–4039. Marsden, S. P.; McGonagle, A. E.; McKeever-Abbas, B. Catalytic Aza-Wittig Cyclizations for Heteroaromatic Synthesis. Org. Lett. 2008, 10, 2589–2591. Tang, X.; Chapman, C.; Whiting, M.; Denton, R. Development of a Redox-Free Mitsunobu Reaction Exploiting Phosphine Oxides as Precursors to Dioxyphosphoranes. Chem. Commun. 2014, 50, 7340–7343. Hellwinkel, D.; Krapp, W. Polycyclische Triaryldioxyphosphorane Extremer Stabilität. Chem. Ber. 1978, 111, 13–41. Kurti, L.; Czako, B. Strategic Applications of Named Reactions in Organic Synthesis; Elsevier: Burlington, 2005.