Enantiocontrolled macrocycle formation by catalytic intramolecular cyclopropanation

Journal of the American Chemical Society

Volumn 122, Issue 24, 2000, Pages 5718-5728

  Doyle, Michael P ^a   Hu, Wenhao ^a   Chapman, Brant ^a   Marnett, Alan B ^a   Peterson, Chad S ^a   Vitale, Justin P ^a   Stanley, Sarah A ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALKENE; ALLYL COMPOUND; AZO COMPOUND; CARBENE; COPPER; CYCLOPROPANE DERIVATIVE; MACROCYCLIC COMPOUND; METHANOL DERIVATIVE; NAPHTHALENE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034697658     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9945414     Document Type: Article

References (47)

1. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1998.
2. Aratani, T. Pure Appl. Chem. 1985, 57, 1839.
3. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
4. (a) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373.
5. (b) Lowenthal, R. E.; Abiko, A.; Masamune, S. Ibid. 1990, 31, 6005.
6. (a) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
7. (b) For a recent application of this catalytic system for the preparation of 3-oxabicyclo[3.1.0]hexan-1-one, see: Fox, M. E.; Li, C.; Marino, J. P., Jr.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 5467.
8. (a) Ito, K.; Yodhitake, M.; Katsuki, T. Heterocycles 1996, 42, 305.
9. (b) Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 1163.
10. Doyle, M. P. Recl. Trav. Chim. Pays-Bas 1991, 110, 305.
11. Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247.
12. (a) Davies, H. M. L.; Bruzinski, P. R.; Lade, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
13. (b) Davies, H. M. L.; Stafford, D. G.; Doan, B. D.; Houser, J. H. Ibid. 1998, 120, 3326.
14. (c) Intramolecular reactions of styryldiazoacetates have been reported: Davies, H. M. L.; Doan, B. D. J. Org. Chem. 1999, 64, 8501.
15. Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1997, 38, 3435.
16. Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H. P.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763.
17. Doyle, M. P.; Kalinin, A. V. J. Org. Chem. 1996, 61, 2179.
18. Rogers, D. H.; Yi, E. C.; Poulter, C. D. J. Org. Chem. 1995, 60, 941.
19. Doyle, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Ruppar, D. A.; Martin, S. F.; Spallar, M. R.; Liras, S. J. Am. Chem. Soc. 1995, 117, 11021.
20. Doyle, M. P.; Peterson, C. S.; Protopopova, M. N.; Marnett, A. B.; Parker. D. L., Jr.; Ene, D. G.; Lynch, V. J. Am. Chem. Soc. 1997, 119, 8826.
21. Doyle, M. P.; Protopopova, M. N.; Poulter, C. D.; Rogers, D. H. J. Am. Chem. Soc. 1995, 117, 7281.
22. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
23. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
24. Doyle, M. P.; Protopopova, M. N. Tetrahedron 1998, 54, 7919.
25. Doyle, M. P.; Peterson, C. S.; Parker, D. L., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1334.
26. (a) Maxwell, J. L.; O'Malley, S.; Brown, K. C.; Kodadek, T. Organometallics 1992, 11, 645.
27. (b) Brown, K. C.; Kodadek, T. J. Am. Chem. Soc. 1992, 114, 8336.
28. Wolf, J. R.; Hamaker, C. G.; Djukic, J. P.; Kodadek, T.; Woo, L. K. J. Am. Chem. Soc. 1995, 117, 9194.
29. Müller, P.; Baud, C.; Ené, D.; Motallebi, S.; Doyle, M. P.; Brandes, B. D.; Dyatkin, A. B.; See, M. M. Helv. Chim. Acta 1995, 78, 459.
30. Kunz, T.; Reissig, H.-U. Tetrahedron Lett. 1989, 30, 2079.
31. (a) Dammast, F.; Reissig, H.-U. Chem. Ber. 1993, 126, 2449.
32. (b) Dammast, F.; Reissig, H.-U. Chem. Ber. 1993, 126, 2727.
33. Schumacher, R.; Dammast, F.; Reissig, H.-U Chem. Eur. J. 1997, 3, 614.
34. Doyle, M. P.; Peterson, C. S.; Zhou, Q. L.; Nishiyama, H. J. Chem. Soc., Chem. Commun. 1997, 211.
35. Doyle, M. P.; Zhou, Q. L.; Dyatkin, A. B.; Ruppar, D. A. Tetrahedron Lett. 1995, 36, 7579.
36. Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. I.; Miertschin, C. S.; Winchester, W. R.; Simonsen, S. H.; Lynch, V.; Ghosh, R. Recl. Trav. Chim. Pays-Bas 1995, 117, 5763.
37. Doyle, M. P.; Zhou, Q. L.; Raab, C. E.; Roos, G. H. P.; Simonsen, S. H.; Lynch, V. Inorg. Chem. 1996, 35, 6064.
38. Doyle, M. P.; Zhou, Q. L.; Simonsen, S. H.; Lynch, V. Synlett 1996, 697.
39. Lo, M. M.-C., Fu, G. C. J. Am. Chem. Soc. 1998, 120, 10270.
40. Doyle, M. P.; Dyatkin, A. B.; Autry, C. L. J. Chem. Soc., Perkin Trans. 1 1995, 619. Stoichiometric production of ketene with 13 and carbon dioxide with 12 provides mass balance.
41. The product originally thought to be that from addition to the internal double bond was actually from oxonium ylide formation with [2,3]-sigmatropic rearrangement: Doyle, M. P.; Peterson, C. S. Tetrahedron Lett. 1997, 38, 5265.
42. Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H. J. Am. Chem. Soc. 1993, 115, 9968-9978.
43. Doyle, M. P.; Eismont, M. E.; Zhou, Q.-L. Russ. Chem. Bull. 1997, 46, 955.
44. Doyle, M. P.; Ene, D. G.; Forbes, D. C.; Pillow, T. J. Chem. Soc., Chem. Commun. 1999, 1691.
45. Boyer, J. H.; Mack, G. H.; Goebel, W.; Morgan, L. R. J. Org. Chem. 1959, 24, 1051-1053.
46. Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. R.; Woerpel, K. A. J. Org. Chem. 1998, 63, 4541-4544.
47. G. J. Kubas Inorg. Synth. 1979, 19, 90-92.