Download e-book for iPad: Selectivity in the Synthesis of Cyclic Sulfonamides: by Kimberly Geoghegan

By Kimberly Geoghegan

ISBN-10: 3319103377

ISBN-13: 9783319103372

ISBN-10: 3319103385

ISBN-13: 9783319103389

In the world of natural chemistry one significant problem we're at the moment confronted with is find out how to gather in all likelihood invaluable molecules in new ways in which generate molecular complexity and in sequences which are as effective as attainable. Our efforts during this regard, particularly for the guidance of amino containing compounds incorporating an fragrant ring, are defined during this doctoral thesis. We found an engaging regioselectivity in an intramolecular Heck response, which we studied for a chain of substrates which are independent by way of the scale of the newly shaped ring, the place very excessive degrees of selectivity in terms of the recent carbon-carbon bond tend to be saw. DFT calculations have been played to aim to make clear the response series. This regioselective Heck response, mixed with the reductive removing of the transitority amino-protecting workforce, allowed us to synthesize the Sceletium alkaloids: mesembrane, mesembranol and mesembrine.

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Extra info for Selectivity in the Synthesis of Cyclic Sulfonamides: Application in the Synthesis of Natural Products

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0 ppm in the 1H NMR spectrum. The same trend is observed in the carbon chemical shifts. In comparison, the substituted alkenyl carbon (in bold) for all compounds have a higher chemical shift in the carbon spectrum, downfield from the neighbouring C–H which is not undergoing C–C bond formation, suggesting that the alkenyl carbon is more electropositive than the methine group. An interesting substrate to attempt our intramolecular Heck cyclisation would be the trimethylsilyl-derivative 199 (Fig. 7), where the TMS-substituent should have a stronger influence on the electronics of the alkene, and consequently might have a different outcome in our intramolecular Heck reaction.

14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. 26. 27. 28. 29. 30. 31. 32. 33. 34. 35. 36. 37. 38. 39. 40. 41. 42. 43. 44. 45. Heck RF, Nolley JPJ (1972) J Org Chem 37:2320 Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581 Heck RF (1982) Org React 27:345 Gibson SE, Middleton RJ (1996) Contemp Org Synth 3:447 Link JT (2002) Org React 60:157 Zeni G, Larock RC (2006) Chem Rev 106:4644 Knowles JP, Whiting A (2007) Org Biomol Chem 5:31 Phan NTS, Van Der Sluys M, Jones CW (2006) Adv Synth Catal 348:609 Oestreich M (ed) (2009) The Mizoroki-Heck reaction.

Herrmann-Beller palladacycle 130) have suggested that nano-particulate colloidal palladium(0) may actually be the active catalyst [34, 35]. It is apparent that the choice of reaction conditions employed and the type of reaction substrate chosen influence the type of palladium(0) complex (123/125, 127 or 128) that N a Pd(0)L2 108 oxidative addition PdLnBr S O2 SO2 CH3 a O2 S b H3C H PdLnBr 123 carbopalladation 124 H3C b N N 122 Neutral a H3C N b O2S BrLnPd H H3C 127 SO2 β-H elim. PdLnBr O2 S β-H elim.

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Selectivity in the Synthesis of Cyclic Sulfonamides: Application in the Synthesis of Natural Products by Kimberly Geoghegan

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