In recent years we have been interested in the chemistry of malonoyl peroxides and their ability to syn-dihydroxylate alkenes1 and oxidize aromatic substrates.2 Based upon an intimate mechanistic understanding of these transformations we have also shown that the bench stable and readily accessible peroxide 1 can be used to bring about a complementary alkene anti-dihydroxylation.3 Building upon this knowledge we were intrigued if 1 could also be used to induce oxidative heterocyclizations. Within this talk we will describe a family of oxidative heterocyclization procedures to prepare biologically relevant saturated heterocycles from readily available precursors. Application of this simple and effective method to the preparation of API Citalopram will also be described. References 1. (a) Griffith, J. C.; Jones, K. M.; Picon, S.; Rawling, M. J.; Kariuki, B. M.; Campbell, M.; Tomkinson, N. C. O. J. Am. Chem. Soc. 2010, 132, 14409. (b) Jones, K. M.; Tomkinson, N. C. O. J. Org. Chem. 2012, 77, 921. (c) Picon, S.; Rawling, M.; Campbell, M.; Tomkinson, N. C. O. Org. Lett. 2012, 14, 6250. (d) Rawling, M. J.; Rowley, J. H.; Campbell, M.; Kennedy, A. R.; Parkinson, J. A.; Tomkinson, N. C. O. Chem. Sci. 2014, 5, 1777. 2. Dragan, A.; Kubczyk, T. M.; Rowley, J. H.; Sproules, S.; Tomkinson. N. C. O. Org. Lett. 2015, 17, 2618. 3. Alamillo-Ferrer, C.; Davidson, S. C.; Rawling, M. J.; Theodoulou, N. H.; Campbell, M.; Humphreys, P. G.; Kennedy, A. R.; Tomkinson, N. C. O. Org. Lett. 2015, DOI: 10.1021/acs.orglett.5b02674.

Oxidative heterocyclizations with malonoyl peroxides

251st National Meeting (2016)

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