New annulations via platinum-catalyzed enyne cyclization and cyclopropane cleavage

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3191-3194

  Nevado, Cristina ^a   Ferrer, Catalina ^a   Echavarren, Antonio M ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CHROMENE DERIVATIVE; CYCLOPROPANE; DIHYDROBENZOFURAN DERIVATIVE; ETHER DERIVATIVE; OXEPANE DERIVATIVE; PLATINUM;

ANNULATION REACTION; ARTICLE; CATALYSIS; CYCLIZATION; CYCLOPROPANATION; OXIDATION; RING OPENING;

EID: 4544324313     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0486573     Document Type: Article

References (31)

1. (a) Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785-6786.
2. (b) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869.
3. (c) Blum, J.; Berr-Kraft, H.; Badrieh, Y. J. Org. Chem. 1995, 60, 5567-5569.
4. (a) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
5. (b) Nevado, C.; Charruault, L.; Michelet, V.; Nieto-Oberhuber, C.; Muñoz, M. P.; Méndez, M.; Rager, M.-N.; Genêt, J. P.; Echavarren, A. M. Eur. J. Org. Chem. 2003, 706-713.
6. (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834.
7. (b) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 215-236.
8. (c) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382.
9. (d) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, in press.
10. Leading references: (a) Park, S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147-149. (b) Braun, N. A.; Spitzner, D. Tetrahedron Lett. 1996, 37, 9187-9188. (c) Kura, K.; Ryu, I.; Kambe, Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521. (d) Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354-4356.
11. Leading references: (a) Park, S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147-149. (b) Braun, N. A.; Spitzner, D. Tetrahedron Lett. 1996, 37, 9187-9188. (c) Kura, K.; Ryu, I.; Kambe, Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521. (d) Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354-4356.
12. Leading references: (a) Park, S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147-149. (b) Braun, N. A.; Spitzner, D. Tetrahedron Lett. 1996, 37, 9187-9188. (c) Kura, K.; Ryu, I.; Kambe, Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521. (d) Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354-4356.
13. Leading references: (a) Park, S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147-149. (b) Braun, N. A.; Spitzner, D. Tetrahedron Lett. 1996, 37, 9187-9188. (c) Kura, K.; Ryu, I.; Kambe, Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520-1521. (d) Murai, S.; Aya, T.; Sonoda, N. J. Org. Chem. 1973, 38, 4354-4356.
14. Pt(II)- and Au(III)-catalyzed methoxycyclization of enol ethers with alkynes: Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635.
15. 4: Oh, C. H.; Bang, S. Y.; Rhim, C. Y. Bull. Korean Chem. Soc. 2003, 24, 887-888.
16. Relative configuration of 6b was determined by X-ray diffraction.
17. Review: Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198.
18. Recent leading references on the oxidative opening of cyclopropanes with metal oxidants: (a) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315-2321. (b) Booker-Milburn, K. I.; Baker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321-15344. (c) Takemoto, Y.; Yamagata, S.; Furose, S.; Hayase, H.; Echigo, T.; Iwata, C. Chem. Commun. 1998, 651-652. (d) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692. (e) Takemoto, Y.; Ibuka, T.; Furuse, S.; Hayase, H.; Echigo, T.; Iwata, C.; Tanaka, T. Chem. Commun. 1999, 2515-2516. (f) Nakamura, M.; Inoue, T.; Nakamura, E. J. Organomet. Chem. 2001, 624, 300-306. (g) Booker-Milburn, K. I.; Jones, J. L.; Sibley, G. E. M.; Cox, R.; Meadows, J. Org. Lett. 2003, 5, 1107-1109.
19. Recent leading references on the oxidative opening of cyclopropanes with metal oxidants: (a) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315-2321. (b) Booker-Milburn, K. I.; Baker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321-15344. (c) Takemoto, Y.; Yamagata, S.; Furose, S.; Hayase, H.; Echigo, T.; Iwata, C. Chem. Commun. 1998, 651-652. (d) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692. (e) Takemoto, Y.; Ibuka, T.; Furuse, S.; Hayase, H.; Echigo, T.; Iwata, C.; Tanaka, T. Chem. Commun. 1999, 2515-2516. (f) Nakamura, M.; Inoue, T.; Nakamura, E. J. Organomet. Chem. 2001, 624, 300-306. (g) Booker-Milburn, K. I.; Jones, J. L.; Sibley, G. E. M.; Cox, R.; Meadows, J. Org. Lett. 2003, 5, 1107-1109.
20. Recent leading references on the oxidative opening of cyclopropanes with metal oxidants: (a) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315-2321. (b) Booker-Milburn, K. I.; Baker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321-15344. (c) Takemoto, Y.; Yamagata, S.; Furose, S.; Hayase, H.; Echigo, T.; Iwata, C. Chem. Commun. 1998, 651-652. (d) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692. (e) Takemoto, Y.; Ibuka, T.; Furuse, S.; Hayase, H.; Echigo, T.; Iwata, C.; Tanaka, T. Chem. Commun. 1999, 2515-2516. (f) Nakamura, M.; Inoue, T.; Nakamura, E. J. Organomet. Chem. 2001, 624, 300-306. (g) Booker-Milburn, K. I.; Jones, J. L.; Sibley, G. E. M.; Cox, R.; Meadows, J. Org. Lett. 2003, 5, 1107-1109.
21. Recent leading references on the oxidative opening of cyclopropanes with metal oxidants: (a) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315-2321. (b) Booker-Milburn, K. I.; Baker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321-15344. (c) Takemoto, Y.; Yamagata, S.; Furose, S.; Hayase, H.; Echigo, T.; Iwata, C. Chem. Commun. 1998, 651-652. (d) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692. (e) Takemoto, Y.; Ibuka, T.; Furuse, S.; Hayase, H.; Echigo, T.; Iwata, C.; Tanaka, T. Chem. Commun. 1999, 2515-2516. (f) Nakamura, M.; Inoue, T.; Nakamura, E. J. Organomet. Chem. 2001, 624, 300-306. (g) Booker-Milburn, K. I.; Jones, J. L.; Sibley, G. E. M.; Cox, R.; Meadows, J. Org. Lett. 2003, 5, 1107-1109.
22. Recent leading references on the oxidative opening of cyclopropanes with metal oxidants: (a) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315-2321. (b) Booker-Milburn, K. I.; Baker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321-15344. (c) Takemoto, Y.; Yamagata, S.; Furose, S.; Hayase, H.; Echigo, T.; Iwata, C. Chem. Commun. 1998, 651-652. (d) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692. (e) Takemoto, Y.; Ibuka, T.; Furuse, S.; Hayase, H.; Echigo, T.; Iwata, C.; Tanaka, T. Chem. Commun. 1999, 2515-2516. (f) Nakamura, M.; Inoue, T.; Nakamura, E. J. Organomet. Chem. 2001, 624, 300-306. (g) Booker-Milburn, K. I.; Jones, J. L.; Sibley, G. E. M.; Cox, R.; Meadows, J. Org. Lett. 2003, 5, 1107-1109.
23. Recent leading references on the oxidative opening of cyclopropanes with metal oxidants: (a) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315-2321. (b) Booker-Milburn, K. I.; Baker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321-15344. (c) Takemoto, Y.; Yamagata, S.; Furose, S.; Hayase, H.; Echigo, T.; Iwata, C. Chem. Commun. 1998, 651-652. (d) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692. (e) Takemoto, Y.; Ibuka, T.; Furuse, S.; Hayase, H.; Echigo, T.; Iwata, C.; Tanaka, T. Chem. Commun. 1999, 2515-2516. (f) Nakamura, M.; Inoue, T.; Nakamura, E. J. Organomet. Chem. 2001, 624, 300-306. (g) Booker-Milburn, K. I.; Jones, J. L.; Sibley, G. E. M.; Cox, R.; Meadows, J. Org. Lett. 2003, 5, 1107-1109.
24. Recent leading references on the oxidative opening of cyclopropanes with metal oxidants: (a) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315-2321. (b) Booker-Milburn, K. I.; Baker, A.; Brailsford, W.; Cox, B.; Mansley, T. E. Tetrahedron 1998, 54, 15321-15344. (c) Takemoto, Y.; Yamagata, S.; Furose, S.; Hayase, H.; Echigo, T.; Iwata, C. Chem. Commun. 1998, 651-652. (d) Kirihara, M.; Ichinose, M.; Takizawa, S.; Momose, T. Chem. Commun. 1998, 1691-1692. (e) Takemoto, Y.; Ibuka, T.; Furuse, S.; Hayase, H.; Echigo, T.; Iwata, C.; Tanaka, T. Chem. Commun. 1999, 2515-2516. (f) Nakamura, M.; Inoue, T.; Nakamura, E. J. Organomet. Chem. 2001, 624, 300-306. (g) Booker-Milburn, K. I.; Jones, J. L.; Sibley, G. E. M.; Cox, R.; Meadows, J. Org. Lett. 2003, 5, 1107-1109.
25. Oxidations of cyclopropane acetals with DDQ or chloranil: (a) Oku, A.; Yamauchi, Y.; Schroeder, M. Chem. Lett. 2001, 1194-1195. (b) Oku, A.; Takahashi, H.; Asmus, S. M. J. Am. Chem. Soc. 2000, 122, 7388-7389. (c) Oku, A.; Abe, M.; Iwamoto, M. J. Org. Chem. 1994, 59, 7445-7452.
26. Oxidations of cyclopropane acetals with DDQ or chloranil: (a) Oku, A.; Yamauchi, Y.; Schroeder, M. Chem. Lett. 2001, 1194-1195. (b) Oku, A.; Takahashi, H.; Asmus, S. M. J. Am. Chem. Soc. 2000, 122, 7388-7389. (c) Oku, A.; Abe, M.; Iwamoto, M. J. Org. Chem. 1994, 59, 7445-7452.
27. Oxidations of cyclopropane acetals with DDQ or chloranil: (a) Oku, A.; Yamauchi, Y.; Schroeder, M. Chem. Lett. 2001, 1194-1195. (b) Oku, A.; Takahashi, H.; Asmus, S. M. J. Am. Chem. Soc. 2000, 122, 7388-7389. (c) Oku, A.; Abe, M.; Iwamoto, M. J. Org. Chem. 1994, 59, 7445-7452.
28. This transformation is presumably initiated by the cleavage of the cyclopropane to form an organolead intermediate. For reviews on electrophilic cyclopropanation: (a) Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625-1647. (b) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. Tetrahedron 2003, 59, 5623-5634.
29. This transformation is presumably initiated by the cleavage of the cyclopropane to form an organolead intermediate. For reviews on electrophilic cyclopropanation: (a) Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625-1647. (b) Taylor, R. E.; Engelhardt, F. C.; Schmitt, M. Tetrahedron 2003, 59, 5623-5634.
30. Retro-Diels-Alder reactions of bicyclo[4.1.0]hept-4-enes: Sellers, S. F.; Dolbier, W. R.; Koroniak, H.; Al-Fekri, D. M. J. Org. Chem. 1984, 49, 1033-1036.
31. Curiously, a 3,4-dihydro-2H-chromene was formed by acid-catalyzed reaction of 13-methoxy-trioxadispiro[4.1.5.3]pentadecane by a mechanism that resembles that proposed for the 21 → 19 and 20 transformation. See: Dorta, R. L.; Martín, A.; Suárez, E. J. Org. Chem. 1997, 62, 2273-2274.