Sulfur ylide-initiated thio-claisen rearrangements. The synthesis of highly substituted indolines

Journal of Organic Chemistry

Volumn 68, Issue 3, 2003, Pages 993-996

  Novikov, Alexei V ^a,b   Kennedy, Abigail R ^a,b,c   Rainier, Jon D ^a,b  

^a University of Arizona   (United States)

^b UNIVERSITY OF UTAH   (United States)

^c EXELIXIS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RHODIUM COMPOUNDS; SULFUR; SYNTHESIS (CHEMICAL); VINYL RESINS;

SIGMATROPIC REARRANGEMENT;

ORGANIC COMPOUNDS;

CARBENOID; INDOLE DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; SYNTHESIS;

CATALYSIS; INDOLES; MOLECULAR STRUCTURE; QUATERNARY AMMONIUM COMPOUNDS; SULFUR;

EID: 0037423350     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026582f     Document Type: Article

References (48)

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2. For recent reviews of indole-containing natural products, see: (a) Lounasmaa, M.; Tolvanen, A. Nat. Prod. Rep. 2000, 17, 175. (b) Faulkner, D. J. Nat. Prod. Rep. 1999, 16, 155.
3. For a recent review covering approaches to the synthesis of indoles, see: Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
4. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175. (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
5. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175. (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
6. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175. (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
7. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175. (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
8. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175. (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
9. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175. (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
10. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175. (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
11. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175. (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
12. For representative examples of the synthesis of indolines having quaternary substitution at C(3) see: (a) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702. (b) Overman, L. E.; Paone, D. V. J. Am. Chem. Soc. 2001, 123, 9465. (c) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) Fischer, C.; Meyers, C.; Carreira, E. M. Helv. Chim. Acta 2000, 83, 1175. (e) Nakazawa, K.; Hayashi, M.; Tanaka, M.; Aso, M.; Suemune, H. Tetrahedron: Asymmetry 2001, 12, 897. (f) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675. (g) Fuji, K.; Kawabata, T.; Ohmori, T. Heterocycles 1998, 47, 951. (h) Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543. (i) Booker-Milburn, K. I.; Fedouloff, M.; Paknoham, S. J.; Strachan, J. B.; Melville, J. L.; Voyle, M. Tetrahedron Lett. 2000, 41, 4657.
13. Kennedy, A. R.; Taday, M. H.; Rainier, J. D. Org. Lett. 2001, 3, 2407.
14. (a) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325.
15. (b) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213.
16. Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V. J. Org. Chem. 1997, 62, 1630.
17. 1H NMR spectroscopy.
18. 1NMR experiments. See Supporting Information for details.
19. For example, the paraherquamides contain spirofused oxindoles analogous to 12. The Williams group has been at the forefront of the synthetic studies towards these agents. See: Williams, R. M.; Cao, J.; Tsujishima, H. Angew. Chem., Int. Ed. 2000, 39, 2540 and references therein.
20. Examples include paraherquamides (see ref 9) and a number of dimeric indoles. The Overman group has been at the forefront of efforts in this latter area. See ref 3b and references therein.
21. Davies, H. M. L.; Clark, D. M.; Alligood, D. B.; Eiband, G. R. Tetrahedron 1987, 43, 4265.
22. There are numerous examples of related reactions. See: Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley & Sons: New York, 1998; 325-336.
23. From the free radical cyclization of (2-isocyanophenylethynyl) trimethylsilane with 2-propanethiol followed by fragmentation coupling with dimethylmalonate. See Supporting Information and ref 5b.
24. (a) Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696.
25. (b) Davies, H. M. L.; Hu, B. Tetrahedron Lett. 1992, 33, 453.
26. (c) Davies, H. M. L.; Hu, B.; Saikali, E.; Bruzinski, P. R. J. Org. Chem. 1994, 59, 4535.
27. For reviews on ylide-initiated cascades (rearrangements and cycloadditions), see: (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (b) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50. (c) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
28. For reviews on ylide-initiated cascades (rearrangements and cycloadditions), see: (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (b) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50. (c) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
29. For reviews on ylide-initiated cascades (rearrangements and cycloadditions), see: (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (b) Hodgson, D. M.; Pierard, F. Y. T. M.; Stupple, P. A. Chem. Soc. Rev. 2001, 30, 50. (c) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
30. For reports from other laboratories of proton transfer to ylide intermediates, see: (a) Padwa, A.; Dean, D. C.; Zhi, L. J. Am. Chem. Soc. 1992, 114, 593. (b) Padwa, A.; Dean, D. C.; Zhi, L. J. Am. Chem. Soc. 1989, 111, 6451. (c) Mori, T.; Sawada, Y.; Oku, A. J. Org. Chem. 2000, 65, 3620.
31. For reports from other laboratories of proton transfer to ylide intermediates, see: (a) Padwa, A.; Dean, D. C.; Zhi, L. J. Am. Chem. Soc. 1992, 114, 593. (b) Padwa, A.; Dean, D. C.; Zhi, L. J. Am. Chem. Soc. 1989, 111, 6451. (c) Mori, T.; Sawada, Y.; Oku, A. J. Org. Chem. 2000, 65, 3620.
32. For reports from other laboratories of proton transfer to ylide intermediates, see: (a) Padwa, A.; Dean, D. C.; Zhi, L. J. Am. Chem. Soc. 1992, 114, 593. (b) Padwa, A.; Dean, D. C.; Zhi, L. J. Am. Chem. Soc. 1989, 111, 6451. (c) Mori, T.; Sawada, Y.; Oku, A. J. Org. Chem. 2000, 65, 3620.
33. While we cannot rule it out at the present time, we disfavor the rearrangement of 33 because it would lead to a highly energetic vinyl anion.
34. We are aware of three other examples of an ylide-initiated [3,3]-sigmatropic rearrangement. See (a) Nakano, H.; Ibata, T. Bull. Chem. Soc. Jpn. 1995, 68, 1393. (b) Wood, J. L.; Moniz, G. A.; Pflum, D. A.; Stoltz, B. M.; Holubec, A. A.; Dietrich, H.-J. J. Am. Chem. Soc. 1999, 121, 1748. (c) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371. (d) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426.
35. We are aware of three other examples of an ylide-initiated [3,3]-sigmatropic rearrangement. See (a) Nakano, H.; Ibata, T. Bull. Chem. Soc. Jpn. 1995, 68, 1393. (b) Wood, J. L.; Moniz, G. A.; Pflum, D. A.; Stoltz, B. M.; Holubec, A. A.; Dietrich, H.-J. J. Am. Chem. Soc. 1999, 121, 1748. (c) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371. (d) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426.
36. We are aware of three other examples of an ylide-initiated [3,3]-sigmatropic rearrangement. See (a) Nakano, H.; Ibata, T. Bull. Chem. Soc. Jpn. 1995, 68, 1393. (b) Wood, J. L.; Moniz, G. A.; Pflum, D. A.; Stoltz, B. M.; Holubec, A. A.; Dietrich, H.-J. J. Am. Chem. Soc. 1999, 121, 1748. (c) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371. (d) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426.
37. We are aware of three other examples of an ylide-initiated [3,3]-sigmatropic rearrangement. See (a) Nakano, H.; Ibata, T. Bull. Chem. Soc. Jpn. 1995, 68, 1393. (b) Wood, J. L.; Moniz, G. A.; Pflum, D. A.; Stoltz, B. M.; Holubec, A. A.; Dietrich, H.-J. J. Am. Chem. Soc. 1999, 121, 1748. (c) Wood, J. L.; Moniz, G. A. Org. Lett. 1999, 1, 371. (d) May, J. A.; Stoltz, B. M. J. Am. Chem. Soc. 2002, 124, 12426.
38. For examples of thio-Claisen rearrangements in indole systems, see: (a) Bycroft, B. W.; Landon, W. J. Chem. Soc., Chem. Commun. 1970, 168. (b) Bycroft, B. W.; Landon, W. J. Chem. Soc., Chem. Commun. 1970, 967.
39. For examples of thio-Claisen rearrangements in indole systems, see: (a) Bycroft, B. W.; Landon, W. J. Chem. Soc., Chem. Commun. 1970, 168. (b) Bycroft, B. W.; Landon, W. J. Chem. Soc., Chem. Commun. 1970, 967.
40. For an example of the use of Claisen rearrangements in the synthesis of oxindoles having quaternary substitution at C(3), see ref 3i.
41. For examples of[1,3]sigmatropic rearrangements in allyl vinyl ethers, see: (a) Grieco, P. A.; Clark, J. D.; Jagoe, C. T. J. Am. Chem. Soc. 1991, 113, 5488. (b) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6891. (c) Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7559. (d) Nonoshita, K.; Banno, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 316.
42. For examples of[1,3]sigmatropic rearrangements in allyl vinyl ethers, see: (a) Grieco, P. A.; Clark, J. D.; Jagoe, C. T. J. Am. Chem. Soc. 1991, 113, 5488. (b) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6891. (c) Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7559. (d) Nonoshita, K.; Banno, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 316.
43. For examples of[1,3]sigmatropic rearrangements in allyl vinyl ethers, see: (a) Grieco, P. A.; Clark, J. D.; Jagoe, C. T. J. Am. Chem. Soc. 1991, 113, 5488. (b) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6891. (c) Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7559. (d) Nonoshita, K.; Banno, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 316.
44. For examples of[1,3]sigmatropic rearrangements in allyl vinyl ethers, see: (a) Grieco, P. A.; Clark, J. D.; Jagoe, C. T. J. Am. Chem. Soc. 1991, 113, 5488. (b) Danishefsky, S.; Funk, R. L.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 6891. (c) Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7559. (d) Nonoshita, K.; Banno, H.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 316.
45. Alternatively, cyclopropanation of the thioindole could be followed by the in situ ring opening of the cyclopropane. Although this mechanism would not be consistent with our results from reactions of other rhodium carbenoids with 2-thioindoles (see ref 4), we cannot rule it out at the present time.
46. While we cannot rule out the possibility that 35 also comes from an ion pair similar to 37, the recombination to form vicinal quaternary substitution is not consistent with such a mechanism.
47. 4 followed by acetonide formation and methylation.
48. Compound 41 comes from the reaction of ClSPh with L-tryptophan methyl ester. See: Crich, D.; Davies, J. W. Tetrahedron Lett. 1989, 30, 4307.