Beyond the corey reaction: One-step diolefination of cyclic ketones

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5689-5696

  Butova, Ekaterina D ^a   Fokin, Andrey A ^a,b   Schreiner, Peter R ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

^b NATIONAL TECHNICAL UNIVERSITY OF UKRAINE   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL GROUP; COREY REACTION; CYCLOUNDECANONE; DIOLEFINATION;

DEPROTONATION; DIMETHYL SULFOXIDE; REACTION KINETICS;

KETONES;

ALKADIENE; BETAINE; CARBONYL DERIVATIVE; CYCLODECANONE; CYCLOHEPTANE DERIVATIVE; CYCLOHEPTANONE; CYCLOPENTANE DERIVATIVE; CYCLOUNDECANONE; DIMETHYLSULFOXONIUM METHYLIDE; ETHYLENE OXIDE; KETONE; KETONE DERIVATIVE; ORGANIC COMPOUND; OXACYCLOPENTANE; OXETANE DERIVATIVE; SODIUM HYDROXIDE; SULFENIC ACID DERIVATIVE; SULFONE DERIVATIVE; SULFOXIDE; TRIMETHYLSULFOXONIUM IODIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COREY METHYLENATION REACTION; DEPROTONATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ANALYSIS; YURCHENKO DIOLEFINATION;

ALKENES; CYCLIZATION; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY;

EID: 34547137364     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070653z     Document Type: Article

References (52)

1. Banti, D.; North, M. Tetrahedron Lett. 2002, 43, 1561-1564;
2. Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757-5762;
3. Johannsen, M.; Jørgensen, K. A. Tetrahedron 1996, 52, 7321-7328;
4. Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667;
5. Kwiatkowski, P.; Asztemborska, M.; Caille, J.-C.; Jurczak, J. Adv. Synth. Catal. 2003, 345, 506-509;
6. Chouraqui, G.; Petit, M.; Phansavath, M.; Aubert, C.; Malacria, M. Eur. J. Org. Chem. 2006, 1413-1421.
7. Gwaltney, S. L., II; Shea, K. J. Tetrahedron Lett. 1996, 37, 949-952;
8. Mori, M.; Tomita, T.; Kita, Y.; Kitamura, T. Tetrahedron Lett. 2004, 45, 4397-4399;
9. Gwaltney, S. L., II; Sakata, S. T.; Shea, K. J. Tetrahedron Lett. 1995, 40, 7177-7180;
10. Nakamura, K.; Yamamura, S. Tetrahedron Lett 1997, 38, 437-438;
11. Faraldos, J. A.; Giner, J.-L. J. Org. Chem. 2002, 67, 4659-4666;
12. Rama Rao, A. V.; Venkatswamy, G.; Javeed, S. M.; Deshpande, V. H.; Ramamohan Rao, B. J. Org. Chem. 1983, 48, 1552-1554;
13. Lambertin, F.; Wende, M.; Quirin, M. J.; Taran, M.; Delmond, B. Eur. J Org. Chem. 1999, 1489-1494.
14. Hopf, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 948-960;
15. Fielder, S.; Rowan, D. D.; Sherburn, M. S. Angew. Chem., Int. Ed. 2000, 39 4331-4333.
16. Kopola, N.; Friess, B.; Cazes, B.; Gore, J. Tetrahedron Lett. 1989, 30, 3963-3966;
17. Kotha, S.; Brahmachary, E.; Sreenivasachary, N. Tetrahedron Lett. 1998, 39, 4095-4098;
18. Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem. Eur. J. 2000, 6, 2435-2448.
19. Alonso, C. M. A.; Neves, M. G. P. M. S.; Tome, A. C.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron Lett. 2000, 41, 5679-5682.
20. Van Straten, J. W.; Van Norden, J. J.; Van Schaik, T. A. M.; Franke, G. T.; De Wolf, W. H.; Bickelhaupt, F. Rec. Trav. Chimiq. Pays-Bas 1978, 97, 105-106;
21. Hegedus, L. S.; Kambe, N.; Ishii, Y.; Mori, A. J. Org. Chem 1985, 50, 2240-2243;
22. Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268-5270;
23. Zhu, L.; Rieke, R. D. Tetrahedron Lett. 1991, 32, 2865-2866;
24. Kinoshita, A.; Sakakibara, N.; Mori, M. J. Am. Chem. Soc. 1997 119, 12388-12389;
25. Lee, S.-J.; Tzeng, C.-B.; Liu, Y.-I.; Chien, C.-J.; Chou, T. J. Org. Chem. 1997, 62, 7812-7819;
26. Chang, H.-M.; Cheng, C.-H. J. Org. Chem. 2000, 65, 1767-1773;
27. Grigg, R.; Kongkathip, N.; Kongkathip, B.; Luangkamin, S.; Dondas, H. A. Tetrahedron 2001, 57, 9187-9197;
28. Alcaide, B.; Almendros, P.; Rodriguez-Acebes, R. J. Org. Chem. 2002, 67, 1925-1928;
29. Oh, C. H.; Sung, H. R.; Park, S. J.; Ahn, K. H. J. Org. Chem. 2002, 67, 7155-7157;
30. Oh, C. H.; Park, S. J. Tetrahedron Lett. 2003, 44, 3785-3787;
31. Oh, C. H.; Jung, S. H.; Park, D. I.; Choi, J. H. Tetrahedron Lett. 2004, 45, 2499-2502;
32. Garst, M. E.; Dolby, L. J.; Esfandiari, S.; Okrent, R. A.; Avey, A. A. J. Org. Chem. 2006, 71, 553-556.
33. Yurchenko, A. G.; Kirii, A. V.; Mel'nik, N. N.; Likhotvorik, I. R.; Zakharsh, P. Zhurn. Org. Khim. 1990, 26, 2230-2231.
34. Yurchenko, A. G.; Kiriy, A. V.; Likhotvorik, I. P.; Melnik, N. N.; Kushko, A. O. Ukr. Khim. Zhurn. 1992, 58, 1106-1116.
35. Yurchenko, A. G.; Kyrij, A. B.; Likhotvorik, I. R.; Melnik, N. N.; Zaharzh, P.; Bzhezovski, V. V.; Kushko, A. O. Synthesis 1991, 393-394.
36. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353-1364.
37. Yurchenko, A. G.; Melnik, N. N.; Likhotvorik, I. R. Tetrahedron Lett. 1989, 30, 3653-3654.
38. Quast, H.; Seefelder, M.; Ivanova, S.; Heubes, M.; Peters, E.-M.; Peters, K. E. Eur. J. Org. Chem. 1999, 3343-3351.
39. Fokin, A. A.; Kushko, A. O.; Kirij, A. V.; Yurchenko, A. G.; Schleyer, P. v. R. J. Org. Chem. 2000, 65, 2984-2995.
40. Okuma, K.; Tanaka, Y.; Kaji, S.; Ohta, H. J. Org. Chem. 1983, 48, 5133-5134.
41. Peng, Y.; Yang, J.-H.; Li, W.-D. Z. Tetrahedron 2006, 62, 1209-1215.
42. Vedejs, E.; Stults, J. S.; Wilde, R. G. J. Am. Chem. Soc. 1988, 110, 5452-5460.
43. Frisch, M. J.; et al. Gaussian 03, Pittsburgh PA 2004.
44. Wodrich, M. D.; Corminboeuf, C.; Schleyer, P. v. R. Org. Lett. 2006, 8, 3631-3634;
45. Grimme, S. Angew. Chem., Int. Ed. 2006, 45, 4460-4464;
46. Schwabe, T.; Grimme, S. Phys. Chem. Chem. Phys. 2006, 8, 4398-4401;
47. Zhao, Y.; Truhlar, D. G. Org. Lett. 2006, 8, 5753-5755;
48. Grimme, S.; Steinmetz, M.; Korth, M. J. Org. Chem. 2007, 72, 2118-2126;
49. Wodrich, M. D.; Corminboeuf, C.; Schreiner, P. R.; Fokin, A. A.; Schleyer, P. v. R. Org. Lett. 2007, 9, 1851-1854.
50. Schreiner, P. R.; Fokin, A. A.; Pascal, R. A.; de Meijere, A. Org. Lett. 2006, 8, 3635-3638.
51. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1345-1353.
52. Bates, R. B.; Gordon, B., III; Highsmith, T. K.; White, J. J. J. Org. Chem. 1984, 49, 2981-2987.