Synthesis of 2-cyclopentenones by gold(I)-catalyzed rautenstrauch rearrangement

Journal of the American Chemical Society

Volumn 127, Issue 16, 2005, Pages 5802-5803

  Shi, Xiaodong ^a   Gorin, David J ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 ETHYNYL 2 PROPENYL ACETATE; ACETIC ACID DERIVATIVE; ALKENE DERIVATIVE; CYCLOPENTENONE; GOLD; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; DIASTEREOISOMER; ISOMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 17744400103     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051689g     Document Type: Article

References (30)

1. Asymmetric Pauson-Khand-type reactions catalyzed by Co: (a) Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron: Asymmetry 2000, 11, 797-808. (b) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 2002, 67, 3398-3403. Ti: (c) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rh: (d) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. (e) Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446-7450. Ir: (f) Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853. For examples of asymmetric Pauson-Khand reaction using chiral auxiliaries, see: (g) Rivero, M. R.; de la Rosa, J. C.; Carretero, J. C. J. Am. Chem. Soc. 2003, 125, 14992 and references therein.
2. Asymmetric Pauson-Khand-type reactions catalyzed by Co: (a) Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron: Asymmetry 2000, 11, 797-808. (b) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 2002, 67, 3398-3403. Ti: (c) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rh: (d) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. (e) Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446-7450. Ir: (f) Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853. For examples of asymmetric Pauson-Khand reaction using chiral auxiliaries, see: (g) Rivero, M. R.; de la Rosa, J. C.; Carretero, J. C. J. Am. Chem. Soc. 2003, 125, 14992 and references therein.
3. Asymmetric Pauson-Khand-type reactions catalyzed by Co: (a) Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron: Asymmetry 2000, 11, 797-808. (b) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 2002, 67, 3398-3403. Ti: (c) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rh: (d) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. (e) Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446-7450. Ir: (f) Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853. For examples of asymmetric Pauson-Khand reaction using chiral auxiliaries, see: (g) Rivero, M. R.; de la Rosa, J. C.; Carretero, J. C. J. Am. Chem. Soc. 2003, 125, 14992 and references therein.
4. Asymmetric Pauson-Khand-type reactions catalyzed by Co: (a) Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron: Asymmetry 2000, 11, 797-808. (b) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 2002, 67, 3398-3403. Ti: (c) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rh: (d) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. (e) Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446-7450. Ir: (f) Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853. For examples of asymmetric Pauson-Khand reaction using chiral auxiliaries, see: (g) Rivero, M. R.; de la Rosa, J. C.; Carretero, J. C. J. Am. Chem. Soc. 2003, 125, 14992 and references therein.
5. Asymmetric Pauson-Khand-type reactions catalyzed by Co: (a) Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron: Asymmetry 2000, 11, 797-808. (b) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 2002, 67, 3398-3403. Ti: (c) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rh: (d) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. (e) Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446-7450. Ir: (f) Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853. For examples of asymmetric Pauson-Khand reaction using chiral auxiliaries, see: (g) Rivero, M. R.; de la Rosa, J. C.; Carretero, J. C. J. Am. Chem. Soc. 2003, 125, 14992 and references therein.
6. Asymmetric Pauson-Khand-type reactions catalyzed by Co: (a) Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron: Asymmetry 2000, 11, 797-808. (b) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 2002, 67, 3398-3403. Ti: (c) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rh: (d) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. (e) Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446-7450. Ir: (f) Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853. For examples of asymmetric Pauson-Khand reaction using chiral auxiliaries, see: (g) Rivero, M. R.; de la Rosa, J. C.; Carretero, J. C. J. Am. Chem. Soc. 2003, 125, 14992 and references therein.
7. Asymmetric Pauson-Khand-type reactions catalyzed by Co: (a) Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron: Asymmetry 2000, 11, 797-808. (b) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 2002, 67, 3398-3403. Ti: (c) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026-7033. Rh: (d) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771-6772. (e) Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446-7450. Ir: (f) Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852-9853. For examples of asymmetric Pauson-Khand reaction using chiral auxiliaries, see: (g) Rivero, M. R.; de la Rosa, J. C.; Carretero, J. C. J. Am. Chem. Soc. 2003, 125, 14992 and references therein.
8. For catalytic asymmetric Nazarov cyclizations, see: (a) Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544. (b) Aggarwal, V. K.; Belfield, A. J. Org. Lett. 2003, 5, 5075. For asymmetric Nazarov cyclizations of chiral allenes, see: (c) Tius, M. A. Acc. Chem. Res. 2003, 36, 284.
9. For catalytic asymmetric Nazarov cyclizations, see: (a) Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544. (b) Aggarwal, V. K.; Belfield, A. J. Org. Lett. 2003, 5, 5075. For asymmetric Nazarov cyclizations of chiral allenes, see: (c) Tius, M. A. Acc. Chem. Res. 2003, 36, 284.
10. For catalytic asymmetric Nazarov cyclizations, see: (a) Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544. (b) Aggarwal, V. K.; Belfield, A. J. Org. Lett. 2003, 5, 5075. For asymmetric Nazarov cyclizations of chiral allenes, see: (c) Tius, M. A. Acc. Chem. Res. 2003, 36, 284.
11. For alternative asymmetric syntheses of cyclopentenones, see: (a) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 10296. (b) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Brillet, C.; Garía-Granda, S.; Piñera-Nicolás, A.; Vázquez, J. T. J. Am. Chem. Soc. 1999, 121, 4516.
12. For alternative asymmetric syntheses of cyclopentenones, see: (a) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 10296. (b) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Brillet, C.; Garía-Granda, S.; Piñera-Nicolás, A.; Vázquez, J. T. J. Am. Chem. Soc. 1999, 121, 4516.
13. Rautenstrauch, V. J. Org. Chem. 1984, 49, 950.
14. (a) Mainetti, E.; Mouriés, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132.
15. (b) Miki, K.; Ohe, K.; Uemura, S. J. Org. Chem. 2003, 68, 8505.
16. (c) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2003, 9, 2627.
17. (d) Mamane, V.; Gress, T.; Krause, H.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 8654.
18. (e) Harrak, Y.; Blasykowski, C.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
19. (a) Neito-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402.
20. (b) Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 10858.
21. (c) Zuang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 11806.
22. (d) Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15978.
23. (e) For an excellent review of homogeneous gold-catalyzed reactions, see: Hashmi, A. S. K. Gold Butt. 2004, 37, 51.
24. (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
25. (b) Staben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350.
26. 2 (100% 4, 0% 5), CuBr (100% 4, 0% 5).
27. Enantioenriched propargyl alcohols were prepared by reduction of the corresponding ketone with R-Alpine-Borane and the absolute stereo-chemistry assigned according to Midland, M. M.; McDowell, D. C.; Hatch, R. L.; Tramontano, A. J. Am. Chem. Soc. 1980, 102, 867.
28. 3)). Hua, D. H. J. Am. Chem. Soc. 1986, 108, 3835. The stereochemistry of the remaining cyclopentenones was assigned by analogy.
29. This transition state also accounts for the observation that rearrangement of a 1:2 mixture of Z:E olefin isomers (34) returned the Z-isomer unreacted. Cyclization of the Z-isomer would require that the olefin substituent come into close proximity to the vinyl gold. (Chemical Equation Presented)
30. In accord with this proposed intermediate, diene 37 was isolated from cycloisomerization of 36. (Chemical Equation Presented)