1 / 51

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

stan
Download Presentation

Vinyl Epoxides in Organic Synthesis

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  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!

More Related