Enantioselective Pictet-Spengler reactions of isatins for the synthesis of spiroindolones

Tetrahedron Letters

Volumn 52, Issue 43, 2011, Pages 5550-5553

  Badillo, Joseph J ^a   Silva García, Abel ^a   Shupe, Benjamin H ^a   Fettinger, James C ^a   Franz, Annaliese K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Chiral Br nsted acid catalysis; Isatin; Pictet Spengler; Spirooxindole

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; INDOLE DERIVATIVE; ISATIN; PHOSPHORIC ACID; SPIROOXINDOLE TETRAHYDRO BETA CARBOLINE; TRYPTAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CONTROLLED STUDY; CYCLIZATION; ENANTIOSELECTIVITY; PICTET SPENGLER REACTION; SYNTHESIS;

EID: 80053181266     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.071     Document Type: Article

References (39)

1. J.J. Badillo, N.V. Hanhan, and A.K. Franz Curr. Opin. Drug Discov. Devel. 13 2010 758 776
2. V. Vintonyak, K. Warburg, H. Kruse, S. Grimme, K. Hübel, D. Rauh, and H. Waldmann Angew. Chem., Int. Ed. 49 2010 5902 5905
3. B.M. Trost, and M.K. Brennan Synthesis 2009 3003 3025
4. C.V. Galliford, and K.A. Scheidt Angew. Chem., Int. Ed. 46 2007 8748 8758
5. S.R. Yong, A.T. Ung, S.G. Pyne, B.W. Skelton, and A.H. White Tetrahedron 63 2007 5579 5586
6. X.-H. Chen, Q. Wei, S.-W. Luo, H. Xiao, and L.-Z. Gong J. Am. Chem. Soc. 131 2009 13819 13825
7. X. Jiang, Y. Cao, Y. Wang, L. Liu, F. Shen, and R. Wang J. Am. Chem. Soc. 132 2010 15328 15333
8. J. Wang, E.A. Crane, and K.A. Scheidt Org. Lett. 13 2011 3086 3089
9. B. Tan, N.R. Candeias, and C.F. Barbas J. Am. Chem. Soc. 133 2011 4672 4675
10. J.J. Badillo, G.E. Arevalo, J.C. Fettinger, and A.K. Franz Org. Lett. 13 2011 418 421
11. W.-B. Chen, Z.-J. Wu, J. Hu, L.-F. Cun, X.-M. Zhang, and W.-C. Yuan Org. Lett. 13 2011 2472 2475
12. B. Tan, G. Hernandez-Torres, and C.F. Barbas J. Am. Chem. Soc. 133 2011 12354 12357
13. B. Tan, N.R. Candeias, and C.F. Barbas Nat. Chem. 3 2011 473 477
14. K. Ding, Y. Lu, Z. Nikolovska-Coleska, G. Wang, S. Qiu, S. Shangary, W. Gao, D. Qin, J. Stuckey, K. Krajewski, P.P. Roller, and S. Wang J. Med. Chem. 49 2006 3432 3435
15. B.K.S. Yeung, B. Zou, M. Rottmann, S.B. Lakshminarayana, S.H. Ang, S.Y. Leong, J. Tan, J. Wong, S. Keller-Maerki, C. Fischli, A. Goh, E.K. Schmitt, P. Krastel, E. Francotte, K. Kuhen, D. Plouffe, K. Henson, T. Wagner, E.A. Winzeler, F. Petersen, R. Brun, V. Dartois, T.T. Diagana, and T.H. Keller J. Med. Chem. 53 2010 5155 5164
16. M. Rottmann, C. McNamara, B.K.S. Yeung, M.C.S. Lee, B. Zou, B. Russell, P. Seitz, D.M. Plouffe, N.V. Dharia, J. Tan, S.B. Cohen, K.R. Spencer, G.E. Gonzalez-Paez, S.B. Lakshminarayana, A. Goh, R. Suwanarusk, T. Jegla, E.K. Schmitt, H.-P. Beck, R. Brun, F. Nosten, L. Renia, V. Dartois, T.H. Keller, D.A. Fidock, E.A. Winzeler, and T.T. Diagana Science 329 2010 1175 1180
17. For recent reviews of Pictet-Spengler reactions, see: J. Stöckigt, A.P. Antonchick, F. Wu, and H. Waldmann Angew. Chem., Int. Ed. 2011 23
18. K. Pulka Curr. Opin. Drug Discov. Devel. 13 2010 669 684
19. E.D. Cox, and J.M. Cook Chem. Rev. 95 1995 1797 1842
20. M.S. Taylor, and E.N. Jacobsen J. Am. Chem. Soc. 126 2004 10558 10559
21. I.T. Raheem, P.S. Thiara, and E.N. Jacobsen Org. Lett. 10 2008 1577 1580
22. R.S. Klausen, and E.N. Jacobsen Org. Lett. 11 2009 887 890
23. J. Seayad, A.M. Seayad, and B. List J. Am. Chem. Soc. 128 2006 1086 1087
24. N.V. Sewgobind, M.J. Wanner, S. Ingemann, R. de Gelder, J.H. van Maarseveen, and H. Hiemstra J. Org. Chem. 73 2008 6405 6408
25. F.R. Bou-Hamdan, and J.L. Leighton Angew. Chem., Int. Ed. 48 2009 2403 2406
26. M.E. Muratore, C.A. Holloway, A.W. Pilling, R.I. Storer, G. Trevitt, and D.J. Dixon J. Am. Chem. Soc. 131 2009 10796 10797
27. C.A. Holloway, M.E. Muratore, R.I. Storer, and D.J. Dixon Org. Lett. 12 2010 4720 4723
28. H. Fang, X. Wu, L. Nie, X. Dai, J. Chen, W. Cao, and G. Zhao Org. Lett. 12 2010 5366 5369
29. While this work was in progress, Bencivenni and co-workers described a related Pictet-Spengler reaction of isatins. In these reports, catalyst (R)-8b was not reported and different substrates and scope were investigated, see: S. Duce, F. Pesciaioli, L. Gramigna, L. Bernardi, A. Mazzanti, A. Ricci, G. Bartoli, and G. Bencivenni Adv. Synth. Catal. 353 2011 860 864
30. N.V. Hanhan, A.H. Sahin, T.W. Chang, J.C. Fettinger, and A.K. Franz Angew. Chem., Int. Ed. 49 2010 744 747
31. For a recent review of chiral phosphoric acid catalysis, see: M. Terada Synthesis 2010 1929 1982
32. The absolute configurations for chiral phosphoric acids in this study are based on products purchased from Sigma-Aldrich. (R)-3,3′-Bis(9- anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate is product #695718 and lot# MKBG2357V was used for these studies with an optical rotation of +139.3 (c = 1%, chloroform), as provided by Sigma-Aldrich. Akiyama and co-workers report [ α ] D 26 -24.9 (c 1.00, EtOH), for the (R)-anthracenyl acid, see: Akiyama, T.; Morita, H.; Fuchibe, K. J. Am. Chem. Soc. 2006, 128, 13070-13071.
33. M. Terada, S. Yokoyama, K. Sorimachi, and D. Uraguchi Adv. Synth. Catal. 349 2007 1863 1867
34. M.J. Wanner, P. Hauwert, H.E. Schoemaker, R. de Gelder, J.H. van Maarseveen, and H. Hiemstra Eur. J. Org. Chem. 2008 180 185
35. Y.-F. Sheng, Q. Gu, A.-J. Zhang, and S.-L. You J. Org. Chem. 74 2009 6899 6901
36. X. Yu, A. Lu, Y. Wang, G. Wu, H. Song, Z. Zhou, and C. Tang Eur. J. Org. Chem. 2011 892 897
37. H. Yamamoto, and K. Futatsugi Angew. Chem., Int. Ed. 44 2005 1924 1942
38. J. Lv, X. Li, L. Zhong, S. Luo, and J.-P. Cheng Org. Lett. 12 2010 1096 1099
39. M. Rueping, R.M. Koenigs, and I. Atodiresei Chem. Eur. J. 16 2010 9350 9365