Titanium-catalyzed stereoselective synthesis of spirooxindole oxazolines

Organic Letters

Volumn 13, Issue 3, 2011, Pages 418-421

  Badillo, Joseph J ^a   Arevalo, Gary E ^a   Fettinger, James C ^a   Franz, Annaliese K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; ISATIN; OXAZOLE DERIVATIVE; SPIRO COMPOUND; TITANIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDOLES; ISATIN; MOLECULAR STRUCTURE; OXAZOLES; SPIRO COMPOUNDS; STEREOISOMERISM; TITANIUM;

EID: 79851476611     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1027305     Document Type: Article

References (30)

1. For recent reviews, see: (a) Badillo, J. J.; Hanhan, N. V.; Franz, A. K. Curr. Opin. Drug Discovery Dev. 2010, 13, 758.
2. (b) Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003.
3. (c) Galliford, C. V.; Scheidt, K. A. Angew, Chem. Int. Ed. 2007, 46, 8748.
4. For recent examples, see: (a) Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron 2007, 63, 5579.
5. (b) Yeung, B. K. S.; Zou, B.; Rottmann, M.; Lakshminarayana, S. B.; Ang, S. H.; Leong, S. Y.; Tan, J.; Wong, J.; Keller-Maerki, S.; Fischli, C.; Goh, A.; Schmitt, E. K.; Krastel, P.; Francotte, E.; Kuhen, K.; Plouffe, D.; Henson, K.; Wagner, T.; Winzeler, E. A.; Petersen, F.; Brun, R.; Dartois, V.; Diagana, T. T.; Keller, T. H. J. Med. Chem. 2010, 53, 5155.
6. (c) Vintonyak, V.; Warburg, K.; Kruse, H.; Grimme, S.; Hübel, K.; Rauh, D.; Waldmann, H. Angew. Chem., Int. Ed. 2010, 49, 5902.
7. (a) Wei, Q.; Gong, L.-Z. Org. Lett. 2010, 12, 1008.
8. (b) Zhang, Y.; Panek, J. S. Org. Lett. 2009, 11, 3366.
9. (a) Westermann, B.; Ayaz, M.; van Berkel, S. S. Angew. Chem., Int. Ed. 2009, 49, 846.
10. (b) Bencivenni, G.; Wu, L.-Y.; Mazzanti, A.; Giannichi, B.; Pesciaioli, F.; Song, M.-P.; Bartoli, G; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7200.
11. (c) Hari Babu, T.; Abragam Joseph, A.; Muralidharan, D.; Perumal, P. T. Tetrahedron Lett. 2010, 51, 994.
12. (d) Jiang, K.; Jia, Z.-J.; Yin, X.; Wu, L.; Chen, Y.-C. Org. Lett. 2010, 12, 2766.
13. Castaldi, M. P.; Troast, D. M.; Porco, J. A. Org. Lett 2009, 11, 3362.
14. (a) Shintani, R.; Hayashi, S.-y.; Murakami, M.; Takeda, M.; Hayashi, T. Org. Lett. 2009, 11, 3754.
15. (b) Lu, C.; Xiao, Q.; Floreancig, P. E. Org. Lett. 2010, 12, 5112.
16. (c) Jiang, X.; Cao, Y.; Wang, Y.; Liu, L.; Shen, F.; Wang, R. J. Am. Chem. Soc. 2010, 132, 15328.
17. (d) Nair, V.; Sethumadhavan, D.; Nair, S. M.; Viji, S.; Rath, N. P. Tetrahedron 2002, 58, 3003.
18. (a) Suga, H.; Fujieda, H.; Hirotsu, Y.; Ibata, T. J. Org. Chem. 1994, 59, 3359.
19. (b) Suga, H.; Shi, X.; Ibata, T. J. Org. Chem. 1993, 58, 7397.
20. (c) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884.
21. (d) Mitchell, J. M.; Shaw, J. T. Angew. Chem., Int. Ed. 2006, 45, 1722.
22. Hanhan, N. V.; Sahin, A. H.; Chang, T. W.; Fettinger, J. C.; Franz, A. K. Angew. Chem., Int. Ed. 2010, 49, 744.
23. For reports of aldehyde cyclizations, diastereoselectivity is dependent on selection of metal, with cis-selectivity observed for Sn (IV) and trans-selectivity observed for Ti (IV) and Al (III) Lewis acids, see reference: Suga, H.; Hirotsu, Y; Fujieda, H.; Ibata, T. Tetrahedron Lett. 1991, 32, 6911.
24. The trans-oxazoline is proposed to result from epimerization of the initial cis-adduct under the reaction conditions. Also see ref 7 for additional details.
25. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952.
26. See Supporting Information for complete experimental details.
27. The calculated ground-state energy difference is based on the B3LYP/6-31+G (d) model of crystal structures for trans-3m and modified cis-3af.
28. (a) Suga, H.; Shi, X.; Ibata, T. Chem. Lett. 1994, 1673.
29. (b) Suga, H.; Shi, X.; Ibata, T.; Kakehi, A. Heterocyclrs 2001, 55, 1711.
30. In an alternate mechanistic pathway, it is envisioned that intermediate 5 may first undergo ring opening to form a nitrilium ion, followed by cyclization to give the observed product.