Cascade synthesis of (E)-2-alkylidenecyclobutanols

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4764-4766

  Falck, J R ^a   Bandyopadhyay, Anish ^a   Puli, Narender ^a   Kundu, Abhijit ^a   Reddy, L Manmohan ^a   Barma, Deb K ^a   He, Anyu ^a   Zhang, Hongming ^b   Kashinath, Dhurke ^c   Baati, Rachid ^c  

^a UNIVERSITY OF TEXAS AT DALLAS   (United States)

^b SOUTHERN METHODIST UNIVERSITY   (United States)

^c UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; CYCLOBUTANOL; KETONE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CYCLOBUTANES; KETONES; STEREOISOMERISM;

EID: 70349911725     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901985c     Document Type: Article

References (46)

1. Review: (a) baati, R.; Falck, J. R.; Mioskowski, C. Actualite Chim. 2009, 326, 25.
2. (b) Baati, R.; Mioskowski, C.; Kashinath, D.; Kodepelly, S.; Lu, B.; Falck, J. R. Tetrahedron Lett. 2009, 50, 402.
3. (c) Bejot, R.; He, A.; Falck, J. R.; Mioskowski, C. Angew. Chem, Int. Ed. 2007, 46, 1719.
4. ~(d) Falck, J. R.; Bejot, R.; Barma, D. K.; Bandyopadhyay, A.; Joseph, S.; Mioskowski, C. J. Org. Chem. 2006, 71, 8178.
5. (e) Falck, J. R.; He, A.; Reddy, L. M.; Kundu, A.; Barma, D. K.; Bandyopadhyay, A.; Kamila, S.; Akella, R.; Bejot, R.; Mioskowski, C. Org. Lett. 2006, 8, 4645.
6. (f) Baati, R.; Mioskowski, C.; Barma, D.; Kache, R.; Falck, J. R. Org. Lett. 2006, 8, 2949.
7. (g) Bejot, R.; Tisserand, S.; Reddy, L. M.; Barma, D. K.; Baati, R.; Falck, J. R.; Mioskowski, C. Angew. Chem., Int. Ed. 2005, 44, 2008.
8. (h) Barma, D. K.; Kundu, A.; Zhang, H.; Mioskowski, C.; Falck, J. R. J. Am. Chem. Soc. 2003, 125, 3218.
9. (i) Barma, D. K.; Kundu, A.; Baati, R.; Mioskowski, C.; Falck, J. R. Org. Lett. 2002, 4, 1387.
10. j) Baati, R.; Barma, D. K.; Falck, J. R.; Mioskowski, C. J. Am. Chem. Soc 2001, 123, 9196.
11. Recent examples: (a) Takai, K.; Toshikawa, S.; Inoue, A.; Kokumai, R.; Hirano, M. J. Organomet. Chem. 2007, 692, 520.
12. (b) Concellon, J. M.; Mejica, C. Eur. J. Org. Chem. 2007, 5250.
13. (c) Nakagawa, M.; Saito, A.; Soga, A.; Yamamoto, N.; Taguchi, T. Tetrahedron Lett. 2005, 46, 5257.
14. ~(d) Takenaka, N.; Xia, G.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 13198.
15. (e) Berkessel, A.; Menche, D.; Sklorz, C. A.; Schroder, M.; Paterson. I. Amgew. Chem., Int. Ed. 2003, 42, 1032.
16. Pospisil, J.; Mueller, C.; Fürstner, A. Chem.-Eur. J. 2009, 15, 5956.
17. (a) Zheng, Y.-B.; Lu, C.-H.; Zheng, Z.-H.; Lin, X.-J.; Su, W.-J.; Shen, Y.-M. Helv. Chim. Acta 2008, 91, 2174.
18. (b) Vasas, A.; Hohmann, J.; Forgo, P.; Szabo, P. Tetrahedron 2004, 60, 5025.
19. (c) Fujiwara, Y.; Naithou, K.; Miyazaki, T.; Hashimoto, K.; Mori, K.; Yamamoto, Y. Tetrahedron Lett. 2001, 42, 2497.
20. Hansen, T. V.; Stenstrom, Y. Naturally Occurring Cyclobutanes. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; Elsevier Science Ltd.: New York, NY, 2001; Vol.5, pp 1-38.
21. (a) Kabalka, G. W.; Yao, M.-L. Tetrahedron Lett. 2003, 44, 7885.
22. ~(b) Fujiwara, T.; Iwasaki, N.; Takeda, T. Chem. Lett. 1998, 741.
23. (bb) Anderson, E. A.; Alexanian, E. J.; Sorensen, E. J. Angew. Chem., Int. Ed. 2004, 43, 1998.
24. (c) Liang, Y.; Jiao, L.; Wang, Y.; Chen, Y.; Ma, L.; Xu, J.; Zhang, S.; Yu, Z.-X. Org. Lett. 2006, 8, 5877.
25. (d) Jung, M. E.; Nishimura, N.; Novack, A. R. J. Am. Chem. Soc. 2005, 127, 11206.
26. (e) Fu, N.-Y.; Chan, S.-H.; Wong, H. N. C. The Application of Cyclobutane Derivatives in Organic Synthesis. In Chemistry of Cyclobutanes; Rappoport, Z., Liebman, J. F., Eds.; John Wiley & Sons Ltd.: Chichester, UK, 2005; Vol.1, pp 357-440.
27. (a) Carreira, E. M.; Hastings, C. A.; Shepard, M. S.; Yerkey, L. A.; Millward, D. B. J. Am. Chem. Soc 1994, 116, 6622.
28. (b) Taylor, D. R.; Warburton, M. R.; Wright, D. B. J. Chem. Soc., Perkin Trans. 1 1972, 1365.
29. (a) Chowdhury, M. A.; Senboku, H.; Tokuda, M. Tetrahedron Lett. 2003, 44, 3329.
30. (b) Bernard, A. M.; Floris, C.; Frangia, A.; Piras, P. P. Synlett 1998, 668.
31. Wu, Z.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 5503.
32. (a) Krohn, K.; Boemer, G. J. Org. Chem. 1994, 59, 6063.
33. (b) AvilaZarraga, J. G.; Maldonado, L. A. Chem. Lett. 2000, 512.
34. (c) Other synthetic methodology: Okuma, K.; Kamahori, Y.; Tsubakihara, K.; Yoshihara, K.; Tanaka, Y.; Shioji, K. J. Org. Chem. 2002, 67, 7355.
35. (d) Mubarak, M. S.; Jennermann, T. R.; Ischay, M.; Peters, D. G. Eur. J. Org. Chem. 2007, 32, 5346.
36. (e) Barbero, A.; Cuadrado, P.; Garcia, C.; Rincon, J. A.; Pulido, F. J. J. Org. Chem. 1998, 63, 7531.
37. (f) Bailey, W. F.; Ovaska, T. V. J. Am. Chem. Soc. 1993, 115, 3080.
38. Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349.
39. 2, column chromatography using a gradient of hexane to hexane/ethyl acetate (10:1) affording 2-alkylidenecyclobutanol 4 in the indicated yields (Table 1).
40. Baati, R.; Barma, D. K.; Falck, J. R.; Mioskowski, C. Tetrahedron lett. 2002, 43, 2183.
41. Comparable enone Cr(II)-reductions are well precedented: (a) Takai, K.; Morita, R.; Toratsu, C. Angew. Chem., Int. Ed 2001, 40, 1116.
42. (b) Toratsu, C.; Fujii, T.; Suzuki, T.; Takai, K. Angew. Chem., Int. Ed. 2000, 39, 2725.
43. (c) Montgomery, D.; Reynolds, K.; Stevenson, P. J. Chem. Soc., Chem. Commun. 1993, 363.
44. Gossage, R. A.; van de Kuil, L. A.; van Koten, G. Acc. Chem. Res. 1998, 31, 423.
45. 2O. Utilization of 2,2-dideuterated 1 led to 4 fully deuterated at the vinyl but nowhere else in the molecule.
46. Vinyl chromium, reagents add to ketones with retention of configuration: Trost, B. M.; Pinkerton, A. B. J. Org. Chem. 2001, 66, 7714.