Allenes and transition metals: A diverging approach to heterocycles

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2245-2248

  Brummond, Kay M ^a   Mitasev, Branko ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CYCLOPENTENONE; HETEROCYCLIC COMPOUND; TRANSITION ELEMENT;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; MOLECULAR MECHANICS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ALKADIENES; ALKYNES; AMINO ACIDS; CYCLIZATION; CYCLOPENTANES; HETEROCYCLIC COMPOUNDS; TRANSITION ELEMENTS;

EID: 3142712364     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0492391     Document Type: Article

References (25)

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2. In some cases, a steric bias can direct the reaction toward the other double bond. (a) Kent, J. L.; Wan, H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407. (b) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931. (c) Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535. (d) Brummond, K. M. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press, Inc.; Stamford, CT, 1999; Vol. 6, p 211. (e) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087. (f) Brummond, K. M.; Lu, J.; Petersen, J. L. J. Am. Chem. Soc. 2000, 122, 4915. Brummond, K. M.; Sill, P.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735.
3. In some cases, a steric bias can direct the reaction toward the other double bond. (a) Kent, J. L.; Wan, H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407. (b) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931. (c) Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535. (d) Brummond, K. M. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press, Inc.; Stamford, CT, 1999; Vol. 6, p 211. (e) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087. (f) Brummond, K. M.; Lu, J.; Petersen, J. L. J. Am. Chem. Soc. 2000, 122, 4915. Brummond, K. M.; Sill, P.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735.
4. In some cases, a steric bias can direct the reaction toward the other double bond. (a) Kent, J. L.; Wan, H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407. (b) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931. (c) Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535. (d) Brummond, K. M. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press, Inc.; Stamford, CT, 1999; Vol. 6, p 211. (e) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087. (f) Brummond, K. M.; Lu, J.; Petersen, J. L. J. Am. Chem. Soc. 2000, 122, 4915. Brummond, K. M.; Sill, P.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735.
5. In some cases, a steric bias can direct the reaction toward the other double bond. (a) Kent, J. L.; Wan, H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407. (b) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931. (c) Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535. (d) Brummond, K. M. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press, Inc.; Stamford, CT, 1999; Vol. 6, p 211. (e) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087. (f) Brummond, K. M.; Lu, J.; Petersen, J. L. J. Am. Chem. Soc. 2000, 122, 4915. Brummond, K. M.; Sill, P.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735.
6. In some cases, a steric bias can direct the reaction toward the other double bond. (a) Kent, J. L.; Wan, H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407. (b) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931. (c) Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535. (d) Brummond, K. M. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press, Inc.; Stamford, CT, 1999; Vol. 6, p 211. (e) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087. (f) Brummond, K. M.; Lu, J.; Petersen, J. L. J. Am. Chem. Soc. 2000, 122, 4915. Brummond, K. M.; Sill, P.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735.
7. In some cases, a steric bias can direct the reaction toward the other double bond. (a) Kent, J. L.; Wan, H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407. (b) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931. (c) Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535. (d) Brummond, K. M. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press, Inc.; Stamford, CT, 1999; Vol. 6, p 211. (e) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087. (f) Brummond, K. M.; Lu, J.; Petersen, J. L. J. Am. Chem. Soc. 2000, 122, 4915. Brummond, K. M.; Sill, P.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735.
8. In some cases, a steric bias can direct the reaction toward the other double bond. (a) Kent, J. L.; Wan, H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407. (b) Brummond, K. M.; Wan, H. Tetrahedron Lett. 1998, 39, 931. (c) Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535. (d) Brummond, K. M. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press, Inc.; Stamford, CT, 1999; Vol. 6, p 211. (e) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087. (f) Brummond, K. M.; Lu, J.; Petersen, J. L. J. Am. Chem. Soc. 2000, 122, 4915. Brummond, K. M.; Sill, P.; Rickards, B.; Geib, S. J. Tetrahedron Lett. 2002, 43, 3735.
9. Brummond, K. M.; Chen, H.; Fisher, K. D.; Kerekes, A. D.; Rickards, B.; Sill, P. C.; Geib, S. J. Org. Lett. 2002, 11, 1931. Brummond, K. M.; Gao, D. Org. Lett. 2003, 5, 3491. Anomalies have been observed, especially if a coordinating group resides near the proximal double bond of the allene, which then directs the reaction to that double bond (unpublished results from our group).
10. Brummond, K. M.; Chen, H.; Fisher, K. D.; Kerekes, A. D.; Rickards, B.; Sill, P. C.; Geib, S. J. Org. Lett. 2002, 11, 1931. Brummond, K. M.; Gao, D. Org. Lett. 2003, 5, 3491. Anomalies have been observed, especially if a coordinating group resides near the proximal double bond of the allene, which then directs the reaction to that double bond (unpublished results from our group).
11. Brummond, K. M.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. Shibata subsequently reported a similar finding: Shibata, T.; Takesue, Y.; Kadowaki, S.; Takagi, K. Synlett 2003, 268.
12. Brummond, K. M.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186. Shibata subsequently reported a similar finding: Shibata, T.; Takesue, Y.; Kadowaki, S.; Takagi, K. Synlett 2003, 268.
13. For preliminary investigations, see: Brummond, K. M.; Chen, H.; Mitasev, B.; Casarez, A. D. Org. Lett. 2004, 6, 0000. Initial disclosure of this type of cyclization: Abstracts of Papers, 226th National Meeting of the American Chemical Society, New York, NY, Sept 7, 2003; American Chemical Society: Washington, DC, 2003. For related observations, see: Makino, T.; Itoh, K. Tetrahedron Lett. 2003, 44, 6335. Makino, T.; Itoh, K. J. Org. Chem. 2004, 69, 395.
14. For preliminary investigations, see: Brummond, K. M.; Chen, H.; Mitasev, B.; Casarez, A. D. Org. Lett. 2004, 6, 0000. Initial disclosure of this type of cyclization: Abstracts of Papers, 226th National Meeting of the American Chemical Society, New York, NY, Sept 7, 2003; American Chemical Society: Washington, DC, 2003. For related observations, see: Makino, T.; Itoh, K. Tetrahedron Lett. 2003, 44, 6335. Makino, T.; Itoh, K. J. Org. Chem. 2004, 69, 395.
15. For preliminary investigations, see: Brummond, K. M.; Chen, H.; Mitasev, B.; Casarez, A. D. Org. Lett. 2004, 6, 0000. Initial disclosure of this type of cyclization: Abstracts of Papers, 226th National Meeting of the American Chemical Society, New York, NY, Sept 7, 2003; American Chemical Society: Washington, DC, 2003. For related observations, see: Makino, T.; Itoh, K. Tetrahedron Lett. 2003, 44, 6335. Makino, T.; Itoh, K. J. Org. Chem. 2004, 69, 395.
16. For preliminary investigations, see: Brummond, K. M.; Chen, H.; Mitasev, B.; Casarez, A. D. Org. Lett. 2004, 6, 0000. Initial disclosure of this type of cyclization: Abstracts of Papers, 226th National Meeting of the American Chemical Society, New York, NY, Sept 7, 2003; American Chemical Society: Washington, DC, 2003. For related observations, see: Makino, T.; Itoh, K. Tetrahedron Lett. 2003, 44, 6335. Makino, T.; Itoh, K. J. Org. Chem. 2004, 69, 395.
17. Bolton, G. L. Tetrahedron Lett. 1996, 37, 3433. Bolton, G. L.; Hodges, J. C.; Rubin, J. R. Tetrahedron 1997, 53, 6611. Bolton, G. L.; Hodges, J. C. J. Comb. Chem. 1999, 1, 130.
18. Bolton, G. L. Tetrahedron Lett. 1996, 37, 3433. Bolton, G. L.; Hodges, J. C.; Rubin, J. R. Tetrahedron 1997, 53, 6611. Bolton, G. L.; Hodges, J. C. J. Comb. Chem. 1999, 1, 130.
19. Bolton, G. L. Tetrahedron Lett. 1996, 37, 3433. Bolton, G. L.; Hodges, J. C.; Rubin, J. R. Tetrahedron 1997, 53, 6611. Bolton, G. L.; Hodges, J. C. J. Comb. Chem. 1999, 1, 130.
20. Castelhano, A. L.; Pliura, D. H.; Taylor, G. J.; Hsieh, K. C.; Krantz, A. J. Am. Chem. Soc. 1984, 106, 2734. Castelhano, A. L.; Horne, S.; Taylor, G. J.; Tetrahedron 1988, 44, 5451.
21. Castelhano, A. L.; Pliura, D. H.; Taylor, G. J.; Hsieh, K. C.; Krantz, A. J. Am. Chem. Soc. 1984, 106, 2734. Castelhano, A. L.; Horne, S.; Taylor, G. J.; Tetrahedron 1988, 44, 5451.
22. Kazmaier, U.; Gorbitz, C. H. Synthesis 1996, 1489.
23. See Supporting Information section for experimental/spectroscopic data for compounds that were not prepared by the authors in refs 7 and 8.
24. Method II could be used to generate the allenic amino acids by increasing the equivalents of LDA (2.5 equiv instead of 1.2 equiv), but the product was formed as a 1:1 mixture of diastereomers. After the Claisen rearrangement, the silicon group was removed.
25. 3.