Chiral cyclopropenyl ketones: Reactive and selective diels-alder dienophiles

Journal of Organic Chemistry

Volumn 78, Issue 7, 2013, Pages 3342-3348

  Fisher, Laural A ^a   Smith, Natalee J ^a   Fox, Joseph M ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER; DIELS-ALDER REACTION; DIENOPHILES; REDUCTIVE OPENING; STEREOGENIC CENTERS; THREE-MEMBERED RINGS;

CHEMICAL REACTIONS;

KETONES;

ALKADIENE; CYCLOPROPENYL KETONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIELS ALDER REACTION;

CYCLOPROPANES; KETONES; MOLECULAR STRUCTURE;

EID: 84875966478     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302683t     Document Type: Article

References (49)

1. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668
2. Wiberg, K. B.; Bartley, W. J. J. Am. Chem. Soc. 1960, 82, 6375
3. Baldwin, J. E.; Reddy, P. J. Org. Chem. 1989, 54, 5264
4. Sodupe, M.; Rios, R.; Branchadell, V.; Nicholas, T.; Oliva, A.; Dannenberg, J. J. J. Am. Chem. Soc. 1997, 119, 4232
5. Jursic, B. S. J. Org. Chem. 1997, 62, 3046
6. Garcia, J. I.; Mayoral, J. A.; Salvatella, L. Acc. Chem. Res. 2000, 33, 658
7. Xidos, J. D.; Gosse, T. L.; Burke, E. D.; Poirier, R. A.; Burnell, D. J. J. Am. Chem. Soc. 2001, 123, 5482
8. Boger, D. L.; Brotherton, C. E. Tetrahedron. 1986, 42, 2777
9. For inverse-electron-demand Diels-Alder reactions of cyclopropenes, see: Thalhammer, F.; Wallfahrer, U.; Sauer, J. Tetrahedron Lett. 1990, 31, 6851
10. For Diels-Alder reactions of tetrahalocyclopropenes, see: Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570 and references cited therein
11. Morandi, B.; Carreria, E. M. Angew. Chem., Int. Ed. 2010, 49, 4294
12. O'Bannon, P. E.; Dailey, W. P. J. Org. Chem. 1991, 56, 2258
13. Ng, W.; Wege, D. Tetrahedron Lett. 1996, 37, 6797
14. Ko, C. C.; Wen, C. W.; Chen, M.-Y.; Chen, W.-G.; Her, M.-C.; Lee, G.-A. Eur. J. Org. Chem. 2007, 953
15. Billups, W. E.; Lee, G.-A.; Arney, B. E.; Whitmire, K. H. J. Am. Chem. Soc. 1991, 113, 7980
16. Sheshenev, A. E.; Baird, M. S.; Croft, A. K.; Starikova, Z. A.; Shashkov, A. S.; Zhuze, A. L.; Bolesov, I. G. Tetrahedron Lett. 2006, 47, 2839
17. Alnes, K. F. S.; Sydnes, L. K. Monatsh. Chem. 2006, 137, 483
18. Sheshenev, A. E.; Baird, M. S.; Croft, A. K.; Bolesov, I. G. Mendeleev Commun. 2004, 299
19. Baird, M. S.; Fitton, H. L.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans. 1 1993, 321
20. Lou, Y.; Horikawa, M.; Kloster, R. A.; Hawryluk, N. A.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916
21. Paulini, K.; Reissig, H.-U. J. Prakt. Chem., Chem. Zeit. 1995, 337, 55
22. Tomilov, Y. V.; Shapiro, E. A.; Protopopova, M. N.; Ioffe, A. I.; Dolgii, I. E.; Nefedov, O. M. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1985, 34, 576
23. Shapiro, E. A.; Lun'kova, G. V.; Nefedov, A. O.; Dolgii, I. E.; Nefedov, O. M. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1981, 30, 2097
24. Wyatt, E. E.; Fergus, S.; Galloway, W. R. J. D.; Bender, A.; Fox, D. J.; Plowright, A. T.; Jessiman, A. S.; Welch, M.; Spring, D. R. Chem. Commun. 2006, 3296
25. Yan, N.; Liu, X.; Pallerla, M. K.; Fox, J. M. J. Org. Chem. 2008, 73, 4283
26. Battiste, M. A. Tetrahedron Lett. 1964, 5, 3795
27. Battiste, M. A. Chem. Ind 1961, 550
28. Battiste, M. A. J. Am. Chem. Soc. 1963, 85, 2175
29. Lind, H.; Deutschman, A. J., Jr. J. Org. Chem. 1967, 32, 326
30. Briones, J. F.; Davies, H. M. L. J. Am. Chem. Soc. 2012, 134, 11916
31. Goto, K.; Takeda, K.; Shimada, N.; Nambu, H.; Anada, M.; Shiro, M.; Ando, K.; Hashimoto, S. Angew. Chem., Int. Ed. 2011, 50, 6803
32. Uehara, M.; Suematsu, H.; Yasutomi, Y.; Katsuki, T. J. Am. Chem. Soc. 2011, 133, 170
33. Cui, X.; Xu, X.; Lu, H.; Zhu, S.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 3304
34. Sims, C. G.; Wege, D. Aust. J. Chem. 1995, 48, 469
35. Dietrich-Buchecker, C.; Martina, D.; Franck-Neumann, M. J. Chem. Res., Synop. 1978, 78
36. Galloway, N.; Dent, B. R.; Halton, B. Aust. J. Chem. 1983, 36, 593
37. Baird, M. S.; Hussain, H. H. J. Chem. Soc., Perkin Trans. 1 1987, 1609
38. Rigby, J. H.; Kierkus, P. C. J. Am. Chem. Soc. 1989, 111, 4125
39. Payne, A. D.; Skelton, B. W.; Wege, D.; White, A. H. Eur. J. Org. Chem. 2007, 1184
40. Magnus, P.; Littich, R. Org. Lett. 2009, 11, 3938
41. Patel, P. R.; Boger, D. L. Org. Lett. 2010, 12, 3540
42. Fisher, L. A.; Fox, J. M. J. Org. Chem. 2008, 73, 8474
43. Diels-Alder reactions of cyclopentadiene with α-alkyl- α,β-unsaturated ketones are poorly stereoselective: Mellor, J. M.; Webb, C. F. J. Chem. Soc., Perkin Trans. 2 1974, 17
44. LaRochelle, R. W.; Trost, B. M.; Krepski, L. J. Org. Chem. 1971, 36, 1126
45. Sauers, R. R.; Sonnet, P. E. Tetrahedron 1964, 20, 1132
46. Lam, J.; Johnson, B. L. Aust. J. Chem. 1972, 24, 2269
47. Liao, L.; Zhang, F.; Yan, N.; Golen, J. A.; Fox, J. M. Tetrahedron 2004, 60, 1803
48. Donaldson, W. A.; Hughes, R. P. J. Am. Chem. Soc. 1982, 104, 4846
49. Cheng, X.; Jiang, X.; Yu, Y.; Ma, S. J. Org. Chem. 2008, 73, 8960