Stereospecific cyclopropanation of highly substituted C-C double bonds promoted by CrCl2. Stereoselective synthesis of cyclopropanecarboxamides and cyclopropyl ketones

Organic Letters

Volumn 9, Issue 16, 2007, Pages 2981-2984

  Concellón, José M ^a   Rodríguez Solla, Humberto ^a   Méjica, Carmen ^a   Blanco, Elena G ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CHLORIDE; CHROMIUM CHLORIDE; CHROMIUM DERIVATIVE; CYCLOPROPANE DERIVATIVE; KETONE; MORPHOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AMIDES; CATALYSIS; CHLORIDES; CHROMIUM COMPOUNDS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; CYCLOPROPANES; KETONES; MOLECULAR STRUCTURE; MORPHOLINES; STEREOISOMERISM;

EID: 34547927263     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070896d     Document Type: Article

References (55)

1. The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1987.
2. (a) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977-1050.
3. (b) Faust, R. Angew. Chem., Int. Ed. 2001, 40, 2251-2253.
4. (c) Donaldson, W. A. Tetrahedron 2001, 57, 8589-8627.
5. (d) Beumer, R.; Reiser, O. Tetrahedron 2001, 57, 6497-6503.
6. (e) Salaün, J. Top. Curr. Chem. 2000, 207, 1-67.
7. (f) Alami, A.; Calnes, M.; Daunis, J.; Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5-24.
8. (g) Liu, H. W.; Walsh, C. T. Biochemistry of the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1987; Chapter 16, pp 959-1025.
9. (a) Breckenridge, R. J.; Suckling, C. J. Tetrahedron 1986, 42, 5665-5677.
10. (b) Arai, Y.; Konno, M.; Shimoji, K.; Konishi, Y.; Niwa, H.; Toda, M.; Hayashi, M. Chem. Pharm. Bull. 1982, 30, 379-382.
11. (a) Katagiri, T.; Iguchi, N.; Kawate, T.; Takahashi, S.; Uneyama, K. Tetrahedron: Asymmetry 2006, 17, 1157-1160.
12. (b) Du, H.; Long, J.; Shi, Y. Org. Lett. 2006, 8, 2827-2829.
13. (c) Long, J.; Du, H.; Li, K.; Shi, Y. Tetrahedron Lett. 2005, 46, 2737-2740.
14. (d) Wipf, P.; Stephenson, C. R. J. Org. Lett. 2005, 7, 1137-1140.
15. (e) Kim, H. Y.; Lurain, A. E.; García-García, P.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2005, 127, 13138-13139.
16. (f) Long, J.; Yuan, Y.; Shi, Y. J. Am. Chem. Soc. 2003, 125, 13632-13633.
17. (g) Aggarwal, V. K.; Fang, G. Y.; Meek, G. Org. Lett. 2003, 5, 4417-4420.
18. (h) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 2003, 125, 2341-2350.
19. (a) Reddy, R. P.; Lee, G. H.; Davies, H. M. L. Org. Lett. 2006, 8, 3437-3440.
20. (b) Bayardon, J.; Holczknecht, O.; Pozzi, G.; Sinou, D. Tetrahedron: Asymmetry 2006, 17, 1568-1572.
21. (c) Branstetter, B.; Hossain, M. M. Tetrahedron Lett. 2006, 47, 221-223.
22. (d) Marko, I. E.; Giard, T.; Sumida, S.; Gies, A.-E. Tetrahedron Lett. 2002, 43, 2317-2320.
23. (a) Deng, X.-M.; Cai, P.; Ye, S.; Sun, X.-L.; Liao, W.-W.; Li, K.; Tang, Y.; Wu, Y.-D.; Dai, L.-X. J. Am. Chem. Soc. 2006, 128, 9730-9740.
24. (b) McCooey, S. H.; McCabe, T.; Connon, S. J. J. Org. Chem. 2006, 71, 1494-1491.
25. (c) Papageorgiou, C. D.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2003, 42, 828-831.
26. (d) Li, A. H.; Dai, L. X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341-2372.
27. (a) Rodríguez, A. D.; Shi, J.-G. Org. Lett. 1999, 1, 337-340.
28. (b) Tanko, J. M.; Phillips, J. P. J. Am. Chem. Soc. 1999, 121, 6078-6079.
29. (c) Enholm, E. J.; Jia, Z. J. J. Org. Chem. 1997, 62, 5248-5249.
30. (d) Mash, E. A.; Gregg, T. M.; Kaczynski, M. A. J. Org. Chem. 1996, 61, 2743-2752.
31. (e) White, J. D.; Jensen, M. S. J. Am. Soc. Chem. 1993, 115, 2970-2971.
32. (a) Yadav, A. K.; Peruncheralathan, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2007, 72, 1388-1394.
33. (b) Tang, Y.; Huang, Y.-Z.; Dai, L.-X.; Sun, J.; Xia, W. J. Org. Chem. 1997, 62, 954-959.
34. (c) Rodriques, K. E. Tetrahedron Lett. 1991, 32, 1275-1278.
35. (d) Artaud, I.; Seyden-Penne, J.; Viout, P. Synthesis 1980, 34-36; and ref 6d.
36. (a) Bhat, N. G.; Garcia, L.; Tamez, V., Jr. Tetrahedron Lett. 2003, 44, 7175-7177.
37. (b) Che, H.; Deng, M.-Z. Org. Lett. 2000, 2, 1649-1651.
38. (c) Pohmakotr, M.; Thisayukta, J. Tetrahedron Lett. 1997, 38, 6759-6762.
39. (d) Nelson, A.; Warren, S. Tetrahedron Lett. 1996, 37, 1501-1504.
40. (e) Shimazaki, M.; Hara, H.; Suzuki, K. Tetrahedron Lett. 1989, 30, 5443-5446.
41. (f) Grignon-Dubois, M.; Dunogues, J.; Calas, R. Synthesis 1976, 737-738.
42. (a) Takai, K.; Hirano, M.; Toshikawa, S. Synlett 2004, 1347-1350.
43. (b) Takai, K.; Toshikawa, S.; Inoue, A.; Kokumai, R. J. Am. Chem. Soc. 2003, 125, 12990-12991.
44. (a) Concellón, J. M.; Rodríguez-Solla, H.; Gómez, C. Angew. Chem., Int. Ed. 2002, 41, 1917-1919.
45. (b) Concellón, J. M.; Rodríguez-Solla, H.; Llavona, R. J. Org. Chem. 2003, 68, 1132-1133.
46. (a) α,β-Unsaturated amides 1 were prepared following the method described in: Concellón, J. M.; Pérez-Andrés, J. A.; Rodriguez-Solla, H. Chem. Eur. J. 2001, 7, 3062-3068.
47. (b) Compounds 1e-g were easily obtained through the amination of cinnamoyl chloride in THF.
48. (c) (Z)-Cinnamamide 1h was obtained from the catalytic Lindlar's hydrogenation of N,N-diethyl-3-phenylpropiolamide.
49. (d) (Z)-Amide 1o was prepared by using the method described in: Concellón, J. M.; Bardales, E. J. Org. Chem. 2003, 68, 9492-9495.
50. 2 was employed (3 equiv) lower yields were obtained (see also Table 1).
51. Morris, D. G. Nuclear Magnetic Resonance and Infrared Spectra of Cyclopropanes and Cyclopropenes. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1987; Chapter 3.
52. Sengupta, S.; Mondai, S.; Das, D. Tetrahedron Lett. 1999, 40, 4107-4110.
53. (a) Mareda, J.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1983, 105, 6997-6999.
54. (b) Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162-7166.
55. This is based on the well-known resonance of the lone pair electron of the nitrogen atom with the carbonyl group. As a consequence of this conjugation the free rotation through the CO-N bond is restricted, being this CO-N bond is shorter than a C-N bond (The Chemistry of Acid Derivatives Patai, S., Ed.; John Wiley and Sons: New York, 1979; Supplement B).