Synthesis of chiral methylenecyclopropane derivatives

Synlett

Volumn , Issue 14, 2005, Pages 2239-2241

  Zohar, Elinor ^a   Stanger, Amnon ^a   Marek, Ilan ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

Allyllithium; Methylenecyclopropane carbinol; Methylenecyclopropanes; Sulfoxide

Indexed keywords

1,1,2 TRIBROMOCYCLOPROPANE; CYCLOPROPANE DERIVATIVE; METHANOL DERIVATIVE; METHYLENECYCLOPROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHIRALITY; DIASTEREOISOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 24744462488     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872247     Document Type: Article

References (56)

1. For reviews, see: (a) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295.
2. (b) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213.
3. (c) Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589.
4. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
5. (e) Goti, A.; Cordero, F. M.; Brandi, A. Top. Curr. Chem. 1996, 178, 1.
6. (f) Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77.
7. (g) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1.
8. (h) Methods of Organic Chemistry (Houben-Weyl), Vol. E17; de Meijere, A., Ed.; Thieme: Stuttgart, 1996.
9. Huang, X.; Zhou, H.; Chen, W. J. Org. Chem. 2004, 69, 839.
10. (a) Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123.
11. (b) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Angew. Chem. Int. Ed. 1999, 38, 3365.
12. (c) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458.
13. (d) Nakamura, I.; Saito, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 2661.
14. (e) Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676.
15. Kawasaki, T.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2002, 67, 4911.
16. Itazaki, M.; Nishihara, Y.; Osakada, K. J. Org. Chem. 2002, 67, 6889.
17. Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Y. K.; Donskaya, N. A.; Tveritinova, E. V.; Yu'reva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069.
18. Chen, Y.; Shi, M. J. Org. Chem. 2004, 69, 426.
19. Scott, M. E.; Han, W.; Lautens, M. Org. Lett. 2004, 6, 3309.
20. (a) Noyori, R.; Takaya, H.; Nakanisi, Y.; Nozaki, H. Can. J. Chem. 1969, 47, 1242.
21. (b) Aratani, T.; Nakanisi, Y.; Nozaki, H. Tetrahedron 1970, 26, 1675.
22. (c) Lautens, M.; Delanghe, P. H. M. J. Am. Chem. Soc. 1994, 116, 8526.
23. (d) Lautens, M.; Ren, Y.; Delanghe, P.; Chiu, P.; Ma, S.; Colucci, J. Can. J. Chem. 1995, 73, 1251.
24. (e) Lautens, M.; Delanghe, P. H. M. J. Org. Chem. 1993, 58, 5037.
25. (f) de Meijere, A.; Wessjohann, L. Synlett 1990, 20.
26. (g) Ramaswany, S.; Prasad, K.; Repic, O. J. Org. Chem. 1992, 57, 6344.
27. (h) Achmatowicz, B.; Kabat, M. M.; Krajewski, J.; Wicha, J. Tetrahedron 1992, 48, 10201.
28. Baldwin, J. E.; Adlington, R. M.; Beddington, D.; Russell, A. T. J. Chem. Soc., Chem. Commun. 1992, 1249.
29. Padwa, A.; Wannamaker, M. W. Tetrahedron 1991, 47, 6139.
30. (a) Zohar, E.; Marek, I. Org. Lett. 2004, 6, 341.
31. (b) Zohar, E.; Ram, M.; Marek, I. Synlett 2004, 1288.
32. Recent synthetically useful reactions of cyclopropenes. Hydrometalation reactions: (a) Rubin, M.; Gevorgyan, V. Synthesis 2004, 796.
33. (b) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2002, 124, 11566.
34. (c) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2003, 125, 7198.
35. (d) Rubina, M.; Rubin, M.; Gevorgyan, V. J. Am. Chem. Soc. 2004, 126, 3688.
36. Carbometalation reactions: (e) Fox, J. M.; Liao, L.-A. J. Am. Chem. Soc. 2002, 124, 14322.
37. (f) Araki, S.; Kenji, O.; Shiraki, F.; Hirashita, T. Tetrahedron Lett. 2002, 43, 8033.
38. Cyclizations and rearrangements: (g) Müller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta 2003, 86, 3164.
39. (h) Ma, S. M.; Zhang, J. L. J. Am. Chem. Soc. 2003, 125, 12386.
40. Cycloadditions: (i) Al Dulayymi, J. R.; Baird, M. S.; Hussain, H. H.; Alhourani, B. J.; Alhabashna, A. M. Y.; Coles, S. J.; Hursthouse, M. B. Tetrahedron Lett. 2000, 41, 4205.
41. (j) Baird, M. S.; Huber, F. A. M.; Clegg, W. Tetrahedron 2001, 57, 9849.
42. (k) Nuske, H.; Brase, S.; de Meijere, A. Synlett 2000, 1467.
43. (l) Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Org. Lett. 2001, 3, 3193.
44. (m) Molchanov, A. P.; Diev, V. V.; Kopf, J.; Kostikov, R. R. Russ. J. Org. Chem. 2004, 40, 431.
45. (n) Orugunty, R. S.; Wright, D. L.; Battiste, M. A.; Helmich, R. J.; Abboud, K. J. Org. Chem. 2004, 69, 406.
46. (o) Orugunty, R. S.; Ghiviriga, I.; Abboud, K. A.; Battiste, M. A.; Wright, D. L. J. Org. Chem. 2004, 69, 570.
47. Ring-opening reactions: (p) Ma, S. M.; Zhang, J. L.; Cai, Y. J.; Lu, L. H. J. Am. Chem. Soc. 2003, 125, 13954.
48. (q) Nakamura, I.; Bajracharya, G. B.; Yamamoto, Y. J. Org. Chem. 2003, 68, 2297.
49. (a) Sklute, G.; Amsallem, D.; Shibli, A.; Varghese, J. P.; Marek, I. J. Am. Chem. Soc. 2003, 125, 11776.
50. (b) Chinkov, N.; Sklute, G.; Chechik, H.; Abramovitch, A.; Amsallem, D.; Varghese, J. P.; Majumdar, S.; Marek, I. Pure Appl. Chem. 2004, 76, 517.
51. Baird, M. S.; Hussain, H. H.; Nethercott, W. J. Chem. Soc., Perkin Trans, 1 1986, 1845.
52. (a) Andersen, K. K.; Gaffield, W.; Papanikolau, N. E.; Foley, J. W.; Perkins, R. I. J. Am. Chem. Soc. 1964, 86, 5637.
53. (b) Solladie, G.; Hutt, J.; Girardin, A. Synthesis 1987, 173.
54. Piffl, M.; Weston, J.; Gunther, W.; Anders, E. J. Org. Chem. 2000, 65, 5942.
55. Stanger, A.; Zohar, E.; Marek, I. unpublished results.
56. 4 and the solvent was removed under reduced pressure. Purification by column chromatography on silica gel (eluent: hexane-EtOAc, 6:1) gave the corresponding methylenecyclopropane in indicated yields.