Protecting-group-free synthesis of 3-tert-prenylated oxindoles: Contiguous all-carbon quaternary centers via tertiary neopentyl substitution

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4485-4487

  Grant, Christopher D ^a   Krlsche, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; PRENYLATION; SYNTHESIS;

CARBON; CATALYSIS; INDOLES; PRENYLATION;

EID: 70349898312     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9018562     Document Type: Article

References (48)

1. For selected reviews encompassing the synthesis and biosynthesis of prenylated indole alkaloids, see: (a) Williams, R. M.; Stocking, E. M.: Sanz-Cervera, J. F. J. F. Curr. Chem 2000, 209, 97.
2. (b) Williams, R. M. Chem. Pharm. Bull. 2002, 50. 711.
3. (c) von Nussbaum. F. Angew. Chem., Int. Ed. 2003, 42, 3068.
4. (d) Williams, R. M.; Cox. R. J. Acc. Chem. Res. 2003, 36, 127.
5. (e) Steffan. N.: Grundmann, A.; Yin, W.-B.; Kremer, A.; Li, S.-M. Curr. Med. Chem. 2009, 16, 218.
6. For application of this strategy toward the synthesis of 3-tertprenylated indoles, see: (a) Amauramine and ardeemin families of natural products: Marsden. S. P.; Depew. K. M.; Danishefsky. S. J. J. Am. Chem. Sag. 1994, 116, 11143.
7. (b) Depew, K. M.: Marsden, S. P.; Zatorska, D.: Zatorski, A.: Bornmann, W. G.; Danishefsky, S. J. Am. Chem. Soc. 1999, 121, 11953.
8. (c) Roquefortine family of natural products: Chen, W.-C.; Joullié, M. M. J. Org. Lett. 1998, 39, 8401.
9. (d) Schiavi. B.: Richard, D. J.; Joullié, M. M. J. Org. Chem. 2002, 67, 620.
10. (e) Richard. D. J.; Schiavi, B.: Joullié. M. M. Proc. Nalt. Acad. Sci. U.S.A. 2004, 101, 11971.
11. (f) Shangguan, N.; Hehre. W. J.; Ohlinger, W. S.; Beavers. M. P.; Joullié, M. M. J. Am. Chem. Soc. 2008, 130, 6281.
12. (g) The oxaline and neoxaline: Sunazuka, T.: Shirahata, T.; Tsuchiya. S.; Hirose, T.; Mori. R.; Harigaya. Y.: Kuwajima, I.; Ohmura, S. Qrg. Lett. 2005, 7, 941.
13. For selected reviews on C-C bond-forming hydrogenation and transfer hydrogenation, see: (a) Ngai. M.-Y.: Kong, J. R.; Krische, M. J. J. Qrg. Chem. 2007, 72, 1063.
14. (b) Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische. M. J. Acc. Chem. Res. 2007, 40, 1394.
15. (c) Shibahara, F.; Krische. M. J. Chem. Lett. 2008, 37. 1102.
16. (d) Bower, J. F.: Kim, I. S.; Patman, R. L.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 34.
17. (a) Skucas, E.; Bower, J. F.: Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12678.
18. (b) Bower. J. F.: Skucas. E.; Patman. R. L.; Krische. M. J. J. Am. Chem. Soc. 2007, 129, 15134.
19. (c) Shibahara, F.; Bower, J. F.; Krische, M. J. Am. Chem. Soc. 2008, 130, 6338.
20. (d) Kim. I. S.: Ngai. M.-Y.; Krische. M. J. J. Am. Chem. Soc. 2008, 130, 6340.
21. (e) Kim. I. S.: Ngai. M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14891.
22. (f) Lu, Y.; Kim, I.-S.; Hassan, A.; Del Valle, D. J.; Krische, M. J. Angew. Chem., Int. Ed. 2009, 48, 5018.
23. (g) Kim, I. S.: Han, S.-B.: Krische, M. J. J. Am. Chem. Soc. 2009, 131, 2514.
24. (h) Han. S.-B.; Kim. I. S.: Han, H.; Krische. M. J. J. Am. Chem. Soc. 2009, 131, 6916.
25. (i) Lu, Y.: Krische, M. J. Org. Lett. 2009, 11, 3108.
26. (j) Hassan. A.; Lu, Y.: Krische, M. J. Org. Lett. 2009, 11, 3112.
27. (k) Itoh, J.: Han, S. B.; Krische, M. Angew. Chem., Int. Ed. 2009, 48, 6316.
28. Nair, V.; Ros, S.; Jayan. C. N.; Viji, S. Synthsis 2003, 2542.
29. (a) Malapel-Andrieu. B.; Piroelle, S.; Mérour, J.-Y. J. Chem. Res. 1998, 594.
30. (b) Kawasaki, T.; Nagaoka, M.; Satoh. T.; Okamoto, A.: Ukon, R.; Ogawa, A. Tetrahedron 2004, 60, 3493.
31. As described in ref 8e, treatment of 3-methyl-3-bromo-oxindole with n-prenyl tributylstannane delivers the 3-methyl-3-tert-prenyl-oxindole in the absence of an N-protecting group. However, stoichiometric quantities of tin byproducts are generated.
32. While many substitution reactions involving C-nucleophiles and 3-substituted-3-halo-oxindoles are reported, examples of tertiary neopentyl substitution are absent. While in earlier literature aza-xylylene intermediates are not proposed as intermediates (e.g. refs a-c), their intervention is possible and highly likely: (a) Labroo, R. B.: Labroo, V. M.; King, M. M.; Cohen, L. A. J. Org. Chem. 1991, 56, 3637.
33. (b) Kobayashi, M.: Aoki, S.: Gato. K.; Matsunami, K.: Kurosu, M.; Kitagawa, I. Chem. Pharm. Bull. 1994, 42, 2449.
34. (c) Rajeswaran. W. G.: Labroo, R. B.; Cohen, L. A. J. Org. Chem. 1999, 64. 1369.
35. (d) Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068.
36. (e) Fuchs, J. R.; Funk, R. L. Org. Lett. 2005. 7, 677.
37. (f) England, D. B.; Merey, G.; Padwa, A. Org. Lett. 2007, 9, 3805.
38. (g) England, D. B.; Merey, G.; Padwa, A. Heterocvcles 2007, 74, 491.
39. (h) Krishna, S.; Stoltz, B. M. tetrahedron. Lett. 2007, 48, 7571.
40. For a seminal observation of substitution reactions involving heteroatom nucleophiles and 3-halo-oxindoles, see: Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 2431. Intervention of aza-xylylene intermediates is not proposed yet is highly probable.
41. For selected examples of primary neopentyl substitution reactions, see: (a) Lewis, R. G.; Gustafson, D. H.; Erman, W. F. Tetrahedron Lett. 1967, 8, 401.
42. (b) Paquette, L. A.; Philips. J. C. Tetrahedron Lett. 1967, 8, 4645.
43. (c) Weiss. R. G.; Snyder, E. I. J. Org. Chem. 1971, 36, 403.
44. (d) Stephenson. B.; Solladie, G.: Mosher, H. S. J. Am. Chem. Soc. 1972, 94, 4184.
45. (e) Anderson, P. H.; Stephenson, B.; Mosher, H. S. J. Am. Chem. Soc. 1974, 96, 3171.
46. For reviews encompassing neopentyl substitution, see: (a) Mosher. H. S. Tetrahedron 1974, 30, 1733.
47. (b) Rossi, R. A.: Postigo, A. I. Curr. Org. Chem. 2003, 7, 747.
48. For ruthenium catalyzed reductive coupling of 1,1-disubstituted alienes to paraformaldehyde and higher aldehydes, see: Ngai, M.-Y.: Skucas, E.; Krische, M. J. Org. Lett. 2008, 10, 2705.