Highly stereoselective Brønsted acid catalyzed synthesis of spirooxindole pyrans

Organic Letters

Volumn 13, Issue 12, 2011, Pages 3086-3089

  Wang, Jingqi ^a   Crane, Erika A ^a   Scheidt, Karl A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PYRAN DERIVATIVE; SPIRO COMPOUND;

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

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE; PYRANS; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 79958821040     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200987c     Document Type: Article

References (54)

1. Mander, L.; Liu, H.-W. Natural Products Structural Diversity II; Elsevier: New York, 2010; Vol. 2.
2. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
3. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
4. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003
5. Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186
6. Galliford, C. V.; Martenson, J. S.; Stern, C.; Scheidt, K. A. Chem. Commun. 2007, 631
7. Nair, V.; Mathai, S.; Augustine, A.; Viji, S.; Radhakrishnan, K. V. Synthesis 2004, 2617
8. Zhang, Y.; Wang, L.; Zhang, M.; Fun, H. K.; Xu, J. H. Org. Lett. 2004, 6, 4893
9. Alcaide, B.; Almendros, P.; Rodriguez-Acebes, R. J. Org. Chem. 2006, 71, 2346
10. Overman, L.; Watson, D. J. Org. Chem. 2006, 71, 2587 and references therein
11. Chen, T.; Xu, X.-P.; Ji, S.-J. J. Comb. Chem. 2010, 12, 659
12. Chen, X.; Wei, Q.; Luo, S.; Xiao, H.; Gong, L. J. Am. Chem. Soc. 2009, 131, 13819
13. Companyó, X.; Zea, A.; Alba, A.-N. R.; Mazzanti, A.; Moyano, A.; Rios, R. Chem. Commun. 2010, 46, 6953
14. Sridhar, R.; Srinivas, B.; Madhav, B.; Reddy, V.; Nageswar, Y.; Rao, K. Can. J. Chem. 2009, 87, 1704
15. Helan, V.; Mills, A.; Drewry, D.; Grant, D. J. Org. Chem. 2010, 75, 6693
16. Nair, V.; Mathai, S.; Mathew, S. C.; Rath, N. P. Tetrahedron 2005, 61, 2849
17. Basavaiah, D.; Rao, J. S.; Reddy, R. J.; Rao, A. J. Chem. Commun. 2005, 2621
18. Babu, T. H.; Karthik, K.; Perumal, P. T. Synlett 2010, 1128
19. Castaldi, M. P.; Troast, D. M.; Porco, J. A. Org. Lett. 2009, 11, 3362 For a related formal [5 + 2] transformation with isatin ketals, see: Zhang, Y.; Panek, J. S. Org. Lett. 2009, 11, 3366
20. Shintani, R.; Hayashi, S.; Murakami, M.; Takeda, M.; Hayashi, T. Org. Lett. 2009, 11, 3754
21. Shintani, R.; Tsuji, T.; Park, S.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 7508
22. Morris, W. J.; Custar, D. W.; Scheidt, K. A. Org. Lett. 2005, 7, 1113
23. Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360
24. Villano, R.; Acocella, M. R.; De Rosa, M.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 2004, 15, 2421
25. Boeckman, R. K.; Pruitt, J. R. J. Am. Chem. Soc. 1989, 111, 8286
26. Boeckman, R. K.; Shao, P. C.; Wrobleski, S. T.; Boehmler, D. J.; Heintzelman, G. R.; Barbosa, A. J. J. Am. Chem. Soc. 2006, 128, 10572
27. Calo, F.; Richardson, J.; Barrett, A. G. M. Org. Lett. 2009, 11, 4910
28. Dritz, J. H.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 5579
29. Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003
30. Seebach, D.; Misslitz, U.; Uhlmann, P. Chem. Ber. 1991, 124, 1845
31. Crane, E. A.; Scheidt, K. A. Angew. Chem., Int. Ed. 2010, 49, 8316
32. Custar, D. W.; Zabawa, T. P.; Hines, J.; Crews, C. M.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 12406
33. Custar, D. W.; Zabawa, T. P.; Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 804
34. Farmer, R. L.; Biddle, M. M.; Nibbs, A. E.; Huang, X.; Bergan, R. C.; Scheidt, K. A. ACS Med. Chem. Lett. 2010, 1, 400
35. da Silva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001, 12, 273
36. Vyas, D. J.; Frohlich, R.; Oestreich, M. J. Org. Chem. 2010, 75, 6720
37. Lai, H.; Huang, Z.; Wu, Q.; Qin, Y. J. Org. Chem. 2008, 74, 283
38. Toullec, P. Y.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2006, 8, 2715
39. Tomita, D.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 6946
40. Nair, V.; Rajesh, C.; Dhanya, R.; Rath, N. P. Tetrahedron Lett. 2002, 43, 5349
41. Smet, M.; Van Oosterwijck, C.; Van Hecke, K.; Van Meervelt, L.; Vandendriessche, A.; Dehaen, W. Synlett 2004, 2388
42. Liang, B.; Kalidindi, S.; Porco, J. A.; Stephenson, C. R. J. Org. Lett. 2010, 12, 572
43. Burke, M. D.; Berger, E. M.; Schreiber, S. L. J. Am. Chem. Soc. 2004, 126, 14095 and references therein
44. Compound 1a and related compounds can be prepared in high ee for some cases; see: Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360
45. De Rosa, M.; Acocelli, M. R.; Villano, R.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 2003, 14, 2499
46. Custar, D. W.; Zabawa, T. P.; Hines, J.; Crews, C. M.; Scheidt, K. A. J. Am. Chem. Soc. 2009, 131, 12406 However, for this study, we employed racemic material. For a report of scandium(III)-catalyzed additions to isatins, see: Hanhan, N. V.; Sahin, A. H.; Chang, T. W.; Fettinger, J. C.; Franz, A. K. Angew. Chem., Int. Ed. 2010, 49, 744
47. 2.
48. Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851
49. Yamamoto, H.; Futatsugi, K. Angew. Chem., Int. Ed. 2005, 44, 1924
50. See the Supporting Information for details and CCDC numbers.
51. Gung, B. W.; Xue, X.; Reich, H. J. J. Org. Chem. 2005, 70, 7232
52. Roush, W. R.; Dilley, G. J. Synlett 2001, 955
53. Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4679 Racemization was not observed in Porco's recent Prins reactions with isatins; see ref 8a
54. We thank Dr. James Leahy (Exelixis) for this suggestion.