Enantiomerically pure cyclohexenones by Fe-mediated carbonylation of alkenyl cyclopropanes [22]

Journal of the American Chemical Society

Volumn 122, Issue 28, 2000, Pages 6807-6808

  Taber, Douglass F ^a   Kanai, Kazuo ^a   Jiang, Qin ^a   Bui, Gina ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; CARBONYL DERIVATIVE; CYCLOPROPANE DERIVATIVE;

COMPLEX FORMATION; ENANTIOMER; LETTER; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0034686684     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994155m     Document Type: Letter

References (39)

1. Undergradutate research participant.
2. (a) The photochemical Fe(CO)5-mediated carbonylation of vinyl cyclopropanes was first reported in 1970: Sarel, S. Acc. Chem. Res. 1978, 11, 204. For more recent references, see:
3. (b) Khusnutdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1.
4. (c) Schulze, M. M.; Gockel, U. Tetrahedron Lett. 1996, 37, 357.
5. (d) Schulze, M. M.; Gockel, U. J. Organomet. Chem. 1996, 525, 155.
6. For an overview of strategies that could be used for the construction of alkenyl cyclopropanes of high enantiomeric purity, sec: (a) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897. For more recent examples, see: (b) Zhou, S.-M.; Deng, M.-Z.; Xia, L.-J. Angew. Chem., Int. Ed. 1998, 37, 2845.
7. For an overview of strategies that could be used for the construction of alkenyl cyclopropanes of high enantiomeric purity, sec: (a) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897. For more recent examples, see: (b) Zhou, S.-M.; Deng, M.-Z.; Xia, L.-J. Angew. Chem., Int. Ed. 1998, 37, 2845.
8. (c) Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 10270
9. (d) Charette, A. B.; Juteau, H.; Lebel, H.; Molinaro, C. J. Am. Chem. Soc. 1998, 120, 11943.
10. (e) Schwarz, J. B.; Meyers, A. I. J. Org. Chem. 1998, 63, 1619.
11. (f) Temme, O.; Taj, S.-A.; Andersson, P. G. J. Org. Chem. 1998, 63, 6007.
12. (g) Sakaguchi, K.; Mano, H.; Ohfune, Y. Tetrahedron Lett. 1998, 39, 4311.
13. (h) Yang, Z.; Lorenz, J. C.; Shi, Y. Tetrahedron Lett. 1998, 39, 8621.
14. (i) Fox, M. E.; Li, C.; Marino, J. P., Jr.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 5467.
15. (j) Dorizon, P.; Su, G.; Ludvig, G.; Nikitina, L.; Paugam, R.; Ollivier, J.; Salaun, J. J. Org. Chem. 1999, 64, 4712.
16. (k) Davies, H. M. L.; Panaro, S. A. Tetrahedron Lett. 1999, 40, 5287.
17. (l) Cai, L.; Mahmoud, H.; Han, Y. Tetrahedron: Asymmetry 1999, 10, 411.
18. For preferential bond "a" opening of alkenyl cyclopropanes, see:
19. (a) Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300.
20. (b) Feldman, K. S.; Bervan, H. M.; Romanelli, A. L.; Parvez, M. J. Org. Chem. 1993, 58, 6851.
21. (c) Feldman, K. S.; Bervan, H. M.; Weinreb, P. H. J. Am. Chem. Soc. 1993, 115, 11364.
22. (d) Takeda, K.; Sakurama, K.; Yoshii, E. Tetrahedron Lett. 1997, 38, 3257.
23. (e) Pattenden, G.; Wiedenau, P. Tetrahedron Lett. 1997, 38, 3647 and references therein.
24. (a) For an overview of carbonylative diene and enyne cyclometalation, see: Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules. 2nd ed.; University Science Books: Sausalito, 1999. For other recent references to carbonylative cyclometalation, see:
25. (b) Taber, D. F.; Wang, Y. J. Am. Chem. Soc. 1997, 119, 22.
26. (c) Zhao, Z.; Ding, Y.; Zhao, G. J. Org. Chem. 1998, 63, 9285.
27. (d) Negishi, E.-I.; Montchamp, J.-L.; Anastasia, L.; Elizarov, A.; Choueiry, D. Tetrahedron Lett. 1998, 39, 2503.
28. (e) Shiu, Y.-T; Madhushaw, R. J.; Li, W.-T.; Lin, Y.-C.; Lee, G.-H.; Peng, S.-M.; Liao, F.-L.; Wang, S.-L.; Liu, R.-S. J. Am. Chem. Soc. 1999, 121, 4066.
29. Concurrently with our work, three other groups reported preferential metal-mediated bond "b" opening of alkenyl cyclopropanes:
30. (a) Murakami, M.; Itami, K.; Ubukata, M.; Tsuji, I.; Ito, Y. J. Org. Chem. 1998, 63, 4.
31. (b) Wender, P. A.; Dyckman, A. J.; Husfield, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442.
32. (c) Trost, B. M ; Toste, F. D.; Shen, H. J. Am. Chem Soc. 2000, 122, 2379.
33. The starting cyclopropanes were mixtures of stereoisomers. Each of the stereoisomers appeared to participate efficiently in the carbonylation reaction.
34. Carda, M.; Van der Eycken, J.; Vandewalle, M. Tetrahedron: Asymmetry 1990, 1, 17.
35. 3MgBr followed by PCC oxidation. On an analytical Chiralcel OD column, eluting with 95:5 hexanes/2-propanol at 1.0 mL/min, 16 (13.5 min) and ent-16 (12.3 min) showed baseline resolution.
36. For leading references to alternative methods for the preparation of 5-alkylcyclohexenones of high enantiomeric purity, see: (a) Asaoka, M.; Shima, K.; Takei, H. Tetrahedron Lett. 1987, 28, 5669.
37. (b) Schwarz, J. B.; Devine, P. N.; Meyers, A. I. Tetrahedron 1997, 53, 8795.
38. (c) Hareau, G. P.-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640.
39. (d) Sarakinos, G.; Corey, E. J. Org. Lett. 1999, 1, 811.