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Vinyl Epoxides in Organic Synthesis

Group Meeting in David’s Group. Vinyl Epoxides in Organic Synthesis. Reporter: Leifeng Wang Supervisor: David Zhigang Wang 2014-06-05. Contents. Background. Synthesis of Vinyl Epoxides 1) Strategy A: From Dienes 2) Strategy B: From Epoxy Aldehydes / Ketones

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Vinyl Epoxides in Organic Synthesis

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  1. Group Meeting in David’s Group Vinyl Epoxides in Organic Synthesis Reporter: Leifeng Wang Supervisor: David Zhigang Wang 2014-06-05

  2. Contents • Background • Synthesis of Vinyl Epoxides • 1) Strategy A: From Dienes • 2) Strategy B: From Epoxy • Aldehydes/Ketones • 3) Strategy C: From Enone/Enal • 4) Strategy D: From Aldehydes • Reactions of Vinyl Epoxides • 1) Nucleophilic Openings • 2) Eliminative Ring-Opening Reactions • 3) Rearrangements • 4) Radical Reactions • 5) Cycloadditions and Formal • Cycloadditions • Summary • Acknowledgment

  3. Background

  4. Contents • Background • Synthesis of Vinyl Epoxides • 1) Strategy A: From Dienes • 2) Strategy B: From Epoxy • Aldehydes/Ketones • 3) Strategy C: From Enone/Enal • 4) Strategy D: From Aldehydes • Reactions of Vinyl Epoxides • 1) Nucleophilic Openings • 2) Eliminative Ring-Opening Reactions • 3) Rearrangements • 4) Radical Reactions • 5) Cycloadditions and Formal • Cycloadditions • Summary • Acknowledgment

  5. Synthesis of Vinyl Epoxides

  6. Strategy A: From Dienes More Electro-Deficient Double Bond More Electro-Rich Double Bond Directed Group Alvarez-Manzaneda, E.; Chahboun, R.; Alvarez, E.; Jose Cano, M.; Haidour, A.; Alvarez-Manzaneda, R. n. Org. Lett. 2010, 12, 4450. Liu, X.; Li, Y.; Wang, G.; Chai, Z.; Wu, Y.; Zhao, G. Tetrahedron: Asymmetry2006, 17, 750. Jogireddy, R.; Maier, M. E. J. Org. Chem. 2006, 71, 6999.

  7. Strategy B: From Epoxy Aldehydes/Ketones Olefination by Wittig-Type Reactions Chandrasekhar, S.; Parida, B. B.; Rambabu, C. J. Org. Chem. 2008, 73, 7826. Olefination by Aldol-Type Condensations Jung, M. E.; Berliner, J. A.; Koroniak, L.; Gugiu, B. G.; Watson, A. D. Org. Lett. 2008, 10, 4207.

  8. Strategy C: From Enone/Enal Corey-ChaykovskyEpoxidation Piccinini, A.; Kavanagh, S. A.; Connon, S. J. Chem. Commun. 2012, 48, 7814. Darzen-Type Reactions Gadaj, A.; Jonczyk, A. Synthesis 2007, 75.

  9. Strategy D: From Aldehydes Corey-ChaykovskyEpoxidation Davoust, M.; Briere, J.-F.; Metzner, P. Org. Biomol. Chem. 2006, 4, 3048 via Halohydrin-Type Intermediates Kang, B.; Britton, R. Org. Lett.2007, 9, 5083.

  10. Contents • Background • Synthesis of Vinyl Epoxides • 1) Strategy A: From Dienes • 2) Strategy B: From Epoxy • Aldehydes/Ketones • 3) Strategy C: From Enone/Enal • 4) Strategy D: From Aldehydes • Reactions of Vinyl Epoxides • 1) Nucleophilic Ring Openings • 2) Rearrangements • 3) Radical Reactions • 4) Cycloadditions and Formal • Cycloadditions • Summary • Acknowledgment

  11. NucleophilicRing Openings

  12. NucleophilicRing Openings—Nitrogen Nucleophiles Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagne,M.R. J. Am. Chem. Soc. 2000, 122, 7905. Lindstrom, U. M.; Olofsson, B.; Somfai, P. Tetrahedron Lett. 1999, 40, 9273. Righi, G.; Manni, L. S.; Bovicelli, P.; Pelagalli, R. Tetrahedron Lett. 2011, 52, 3895.

  13. NucleophilicRing Openings—Nitrogen Nucleophiles Chandrasekhar, S.; Parida, B. B.; Rambabu, C. J. Org. Chem. 2008, 73, 7826. Yaragorla, S.; Muthyala, R. Tetrahedron Lett. 2010, 51, 467.

  14. NucleophilicRing Openings—Oxygen Nucleophiles Gomez, A. M.; Pedregosa, A.; Uriel, C.; Valverde, S.; Lopez, J. C. Eur. J. Org. Chem. 2010, 5619. Buchanan, G. S.; Cole, K. P.; Tang, Y.; Hsung, R. P. J. Org. Chem. 2011, 76, 7027.

  15. NucleophilicRing Openings—Oxygen Nucleophiles Yu, X.-Q.; Hirai, A.; Miyashita, M. Chem. Lett. 2004, 33, 764. Uchida, K.; Yokoshima, S.; Kan, T.; Fukuyama, T. Org. Lett. 2006, 8, 5311.

  16. NucleophilicRing Openings—Oxygen Nucleophiles Nicolaou, K. C.; Nakamura, T. M. B. T. J. Am. Chem. Soc.2011, 133, 220. Nicolaou, K. C.; Seo, J. H.; Nakamura, T.; Aversa, R. J. J. Am. Chem. Soc. 2011, 133, 214. Fukui, H.; Shiina, I. Org. Lett. 2008, 10, 3153.

  17. NucleophilicRing Openings—Sulfur Nucleophiles Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagne,M.R. J. Am. Chem. Soc. 2000, 122, 7905. Fedorov, A.; Fu, C.; Linden, A.; Heimgartner, H. Eur. J. Org. Chem. 2005, 1613.

  18. NucleophilicRing Openings—Halide Nucleophiles Hunter, L.; Kirsch, P.; Slawin, A. M. Z.; O’Hagan, D. Angew. Chem. Int. Ed. 2009, 48, 5457. Murakami, T.; Shimizu, T.; Taguchi, K. Tetrahedron2000, 56, 533.

  19. NucleophilicRing Openings—Halide Nucleophiles Usami, Y.; Ohsugi, M.; Mizuki, K.; Ichikawa, H.; Arimoto, M. Org. Lett.2009, 11, 2699. Buchanan, G. S.; Cole, K. P.; Tang, Y.; Hsung, R. P. J. Org. Chem. 2011, 76, 7027.

  20. NucleophilicRing Openings—Hydride Nucleophiles Gowrisankar, P.; Pujari, S. A.; Kaliappan, K. P. Chem. Eur. J. 2010, 16, 5858. Ma, K.; Zhang, C.; Liu, M.; Chu, Y.; Zhou, L.; Hu, C.; Ye, D. Tetrahedron Lett. 2010, 51, 1870.

  21. NucleophilicRing Openings—Carbon Nucleophiles Friedel-Crafts-Type Reactions Ono, M.; Suzuki, K.; Akita, H. Tetrahedron Lett. 1999, 40, 8223. Alkenes Myers, A. G.; Siu, M. Tetrahedron2002, 58, 6397. Enolate Lovchik, M. A.; Frater, G.; Goeke, A.; Hug, W. Chem. Biodiversity 2008, 5, 126.

  22. NucleophilicRing Openings—Carbon Nucleophiles Mahapatra, S.; Carter, R. G. Org. Biomol. Chem. 2009, 7, 4582. Xie, X.; Yue, G.; Tang, S.; Huo, X.; Liang, Q.; She, X.; Pan, X. Org. Lett. 2005, 7, 4057. Di Bussolo, V.; Caselli, M.; Romano, M. R.; Pineschi, M.; Crotti, P. J. Org. Chem. 2004, 69, 8702.

  23. Rearrangements Pericyclic Reactions Boyd, D. R.; Sharma, N. D.; Llamas, N. M.; O’Dowd, C. R.; Allen, C. C. R. Org. Biomol. Chem. 2007, 5, 2267. Meinwald Rearrangements Deng, X.-M.; Sun, X.-L.; Tang, Y. J. Org. Chem. 2005, 70, 6537 Ring Expansion Rearrangements Brichacek, M.; Batory, L. A.; Njardarson, J. T. Angew. Chem., Int. Ed. 2010, 49, 1648.

  24. Radical Reactions Reactions of Alkoxy Radicals Ogawa, Y.; Kuroda, K.; Mukaiyama, T. Chem. Lett. 2005, 34, 698.

  25. Radical Reactions Reactions of Carbon Radicals Feldman, K. S.; Fisher, T. E. Tetrahedron 1989, 45, 2969. Reactions of Allylic Radicals Yadav, J. S.; Srinivas, D.; Shekharam, T. Tetrahedron Lett. 1994, 35, 3625.

  26. Cycloadditions and Formal Cycloadditions

  27. Cycloadditions and Formal Cycloadditions (3 + 2) Cycloadditions Yıldırım, M.; Durust, Y. Tetrahedron2011, 67, 3209. Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123

  28. Cycloadditions and Formal Cycloadditions (4 + 2) Cycloadditions Pale, P.; Bouquant, J.; Chuche, J.; Carrupt, P. A.; Vogel, P. Tetrahedron 1994, 50, 8035. (4 + 3) Cycloadditions Liu, L. L.; Chiu, P. Chem. Commun.2011, 47, 3416 (5 + 2) Cycloadditions Feng, J.-J.; Zhang, J. J. Am. Chem. Soc. 2011, 133, 7304.

  29. Summary

  30. Thank you for your attention!

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