Tetrazolic acid functionalized dihydroindol: Rational design of a highly selective cyclopropanation organocatalyst

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5874-5877

  Hartikka, Antti ^a   Arvidsson, Per I ^a,b  

^a UPPSALA UNIVERSITY   (Sweden)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CYCLIZATION; ENANTIOSELECTIVITY; PROPANE; SATURATION (MATERIALS COMPOSITION); SULFUR;

CYCLOPROPANATION; ORGANOCATALYSTS; UNSATURATED ALDEHYDES;

CATALYSTS;

ALDEHYDE; CYCLOPROPANE; INDOLE DERIVATIVE; INDOLIN 2 YL 1H TETRAZOLE; ORGANIC COMPOUND; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLOPROPANATION; ENANTIOMER; GAS LIQUID CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 34547098110     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070519e     Document Type: Article

References (59)

1. A thorough review has been published on the topic: Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
2. (a) Hennion, G. F.; Sheehan, J. J. J. Am. Chem. Soc. 1949, 71, 1964.
3. (b) Wittig, G.; Wingler, F. Justus Liebigs Ann. Chem. 1961, 650, 18.
4. (c) Wittig, G.; Schwarzenbach, K. Angew. Chem. 1959, 71, 652.
5. (d) Takai, K.; Kakiuchi, T.; Utimoto, K. J. Org. Chem. 1994, 59, 2671.
6. (a) Winstein, S.; Sonnenberg, J.; De Vries, L. J. Am. Chem. Soc. 1959, 81, 6523.
7. (b) Winstein, S.; Sonnenberg, J. J. Am. Chem. Soc. 1961, 83, 3235.
8. (c) Hoveyda, A. H.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
9. (d) Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1990, 112, 6429.
10. (e) Charette, A. B.; Lebel, H. J. Org. Chem. 1995, 60, 2966.
11. (a) Charette, A. B.; Côté, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166.
12. (b) Mash, F. A.; Nelson, K. A. J. Am. Chem. Soc. 1985, 107, 8256.
13. (c) Seebach, D.; Stucky, G. Angew. Chem., Int. Ed. 1988, 27, 1351.
14. (a) Imai, N.; Sakamoto, K.; Takahashi, H.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 7045.
15. (b) Imai, N.; Takahashi, H.; Kobayashi, S. Chem. Lett. 1994, 177.
16. (c) Denmark, S. E.; O'Connor, S. P.; Wilson, S. R. Angew. Chem., Int. Ed. 1998, 37, 1149.
17. (d) Denmark, S. E.; O'Connor, S. P. J. Org. Chem. 1997, 62, 584.
18. (a) Charette, A. B.; Brochu, C. J. Am. Chem. Soc. 1995, 117, 11367.
19. (b) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12168.
20. (c) A recent paper reported on Enantioselective Cyclopropanation with TADDOL-Derived Phosphate Ligands, see: Charette, A. B.; Voituriez, A. Adv. Synth. Catal 2006, 348, 16-17, 2363.
21. (a) Artaud, I.; Seyden-Penne, J.; Viout, P. Synthesis 1980, 34.
22. (b) Hudlicky, T.; Radesca, L.; Luna, H.; Anderson, F. E. J. Org. Chem. 1986, 51, 4746.
23. (c) Caine, D. Tetrahedron 2001, 57, 2643.
24. Hakam, K.; Thielman, M.; Thielman, T.; Winterfeldt, E. Tetrahedron 1987, 43, 2035.
25. (a) Krollpfeiffer, F.; Hartmann, H. Chem. Ber. 1950, 83, 90.
26. (b) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867.
27. (c) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.
28. Bestmann, H. J.; Seng, F. Angew. Chem. 1962, 74, 154.
29. Huang, Y.-Z.; Shen, Y. Adv. Organomet. Chem. 1982, 20, 115.
30. Huang, Y.-Z.; Yong, T.; Zhou, Z.-L. Tetrahedron 1998, 54, 1667.
31. Papageorgiou, C. D.; Cubillo de Dios, M. A.; Ley, S. V.; Gaunt, M. J. Angew. Chem., Int. Ed. 2004, 43, 4641.
32. Kunz, R. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3240.
33. For a thorough review of the topic see: Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379.
34. Cobb, A. J. A.; Shaw, D. M.; Ley, S. V. Synlett 2004, 3, 558.
35. Torii, H.; Nakadai, M.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem., Int. Ed. 2004, 43, 1983.
36. (a) Hartikka, A.; Arvidsson, P. I. Tetrahedron: Asymmetry 2004, 15, 1831.
37. (b) Hartikka, A.; Arvidsson, P. I. Eur. J. Org. Chem. 2005, 4287.
38. (a) Dodda, R.; Zhao, C.-G. Org. Lett. 2006, 8, 21, 4911.
39. (b) Kumarn, S.; Shaw, D. M.; Ley, S. V. Chem. Commun. 2006, 30, 3211.
40. (c) Chowdari, N, S.; Ahmad, M.; Albertshofer, K.; Tanaka, F.; Barbas, C. F., III Org. Lett. 2006, 8, 2839.
41. (d) Mitchell, C. E. T.; Brenner, S. E.; Garcia-Fortanet, J.; Ley, S. V. Org. Biomol. Chem. 2006, 4, 2039.
42. (e) Samanta, S.; Zhao, C.-G. Tetrahedron Lett. 2006, 47, 3383.
43. (f) Suri, J. T.; Mitsumori, S.; Albertshofer, K.; Tanaka, F.; Barbas, C. F., III J. Org. Chem. 2006, 71, 3822.
44. (g) Limbach, M. Chem. Biodiversity 2006, 3, 119.
45. (h) Knudsen, K. R.; Mitchell, C. E. T.; Ley, S. V. Chem. Commun. 2006, 1, 66.
46. (i) Ibrahem, I.; Zou, W.; Casas, J.; Sunden, H.; Cordova, A. Tetrahedron 2006, 62, 357.
47. (j) Grondal, C.; Enders, D. Tetrahedron 2006, 62, 329.
48. (k) Mitchell, C. E. T.; Brenner, S. E.; Ley, S. V. Chem. Commun. 2005, 42, 5346.
49. (l) Sunden, H.; Ibrahem, I.; Eriksson, L.; Cordova, A. Angew. Chem., Int. Ed. 2005, 44, 4877.
50. (m) Kumarn, S.; Shaw, D. M.; Longbottom, D. A.; Ley, S. V. Org. Lett. 2005, 7, 4189.
51. Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861.
52. Bergmann, M.; Zervas, L. Chem. Ber. 1932, 65, 1192.
53. (a) Pozdnev, V. F. Tetrahedron Lett. 1995, 36, 7115.
54. (a) Spero, D. M.; Kapadia, S. R. J. Org. Chem. 1996, 61, 7398.
55. (b) Olah, G. A.; Narang, S.; Fung, A. P.; Gupta, G. B. Synthesis 1980, 8, 657.
56. (a) Demko, Z. P.; Sharpless, K. B. Org. Lett. 2002, 4, 2525.
57. (b) Huisgen, R. Pure Appl. Chem. 1989, 61, 613.
58. Almquist, G. R.; Chao, W.; White-Jennings, C. J. Med. Chem. 1985, 28, 1067.
59. Both catalytic systems were assessed as in the previous report (ref 14), which allowed correlation of the relative and absolute stereochemistry of products generated by catalyst (1) from the retention time of products in GC or HPLC generated from catalytic system 2.