Ionic nucleophilic catalysis of chiral ammonium betaines for highly stereoselective aldol reaction from oxindole-derived vinylic carbonates

Journal of the American Chemical Society

Volumn 134, Issue 16, 2012, Pages 6972-6975

  Uraguchi, Daisuke ^a   Koshimoto, Kyohei ^a   Ooi, Takashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATING AGENTS; ALDOL REACTIONS; BOND-FORMING REACTIONS; ELECTROPHILES; ENANTIOSELECTIVE; ENOLATES; NUCLEOPHILIC CATALYSIS; STEREO-SELECTIVE; SYNTHETIC UTILITY;

CARBONATES; CATALYSIS; CONDENSATION REACTIONS; STEREOSELECTIVITY;

AMMONIUM COMPOUNDS;

AMMONIA; BETAINE DERIVATIVE; CARBON; CARBONIC ACID DERIVATIVE; ELECTROPHILE; ESTER; OXINDOLE; VINYL DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; HYDROLYSIS; NUCLEOPHILICITY; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

BETAINE; CARBONATES; CATALYSIS; INDOLES; IONS; MOLECULAR STRUCTURE; QUATERNARY AMMONIUM COMPOUNDS; STEREOISOMERISM;

EID: 84860319209     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3022939     Document Type: Article

References (49)

1. Flematti, G. R.; Ghisalberti, E. L.; Dixon, K. W.; Trengove, R. D. Science 2004, 305, 977
2. Appendino, G.; Prosperini, S.; Valdivia, C.; Ballero, M.; Colombano, G.; Billington, R. A.; Genazzani, A. A.; Sterner, O. J. Nat. Prod. 2005, 68, 1213
3. Saouf, A.; Guerra, F. M.; Rubal, J. J.; Moreno-Dorado, F. J.; Akssira, M.; Mellouki, F.; López, M.; Pujadas, A. J.; Jorge, Z. D.; Massanet, G. M. Org. Lett. 2005, 7, 881
4. Commeiras, L.; Thibonnet, J.; Parrain, J.-L. Org. Biomol. Chem. 2009, 7, 425
5. Chenevert, R.; Pelchat, N.; Jacques, F. Curr. Org. Chem. 2006, 10, 1067
6. Bruneau, C.; Neveux, M.; Kabouche, Z.; Ruppin, C.; Dixneuf, P. H. Synlett 1991, 755
7. Husár, B.; Liska, R. Chem. Soc. Rev. 2012, 41, 2395
8. Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357
9. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1999, 121, 892
10. Yanagisawa, A.; Matsumoto, Y.; Asakawa, K.; Yamamoto, H. Tetrahedron 2002, 58, 8331
11. Izumiseki, A.; Yoshida, K.; Yanagisawa, A. Org. Lett. 2009, 11, 5310
12. Claraz, A.; Leroy, J.; Oudeyer, S.; Levacher, V. J. Org. Chem. 2011, 76, 6457
13. Yamamoto, E.; Nagai, A.; Hamasaki, A.; Tokunaga, M. Chem.-Eur. J 2011, 17, 7178
14. Mohr, J. T.; Stoltz, B. M. Chem.-Asian J. 2007, 2, 1476
15. Trost, B. M.; Lehr, K.; Michaelis, D. J.; Xu, J.; Buckl, A. K. J. Am. Chem. Soc. 2010, 132, 8915
16. Behenna, D. C.; Mohr, J. T.; Sherden, N. H.; Marinescu, S. C.; Harned, A. M.; Tani, K.; Seto, M.; Ma, S.; Novák, Z.; Krout, M. R.; McFadden, R. M.; Roizen, J. L.; Enquist, J. A.; White, D. E.; Levine, S. R.; Petrova, K. V.; Iwashita, A.; Virgil, S. C.; Stoltz, B. M. Chem.-Eur. J. 2011, 17, 14199
17. Trost, B. M.; Michaelis, D. J.; Charpentier, J.; Xu, J. Angew. Chem., Int. Ed. 2012, 51, 204
18. Moyano, A.; El-Hamdouni, N.; Atlamsani, A. Chem.-Eur. J 2010, 16, 5260
19. Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 11532
20. Shaw, S. A.; Aleman, P.; Vedejs, E. J. Am. Chem. Soc. 2003, 125, 13368
21. Seitzberg, J. G.; Dissing, C.; Søtofte, I.; Norrby, P.-O.; Johannsen, M. J. Org. Chem. 2005, 70, 8332
22. Shaw, S. A.; Aleman, P.; Christy, J.; Kampf, J. W.; Va, P.; Vedejs, E. J. Am. Chem. Soc. 2006, 128, 925
23. Nguyen, H. V.; Butler, D. C. D.; Richards, C. J. Org. Lett. 2006, 8, 769
24. Busto, E.; Gotor-Fernández, V.; Gotor, V. Adv. Synth. Catal. 2006, 348, 2626
25. Joannesse, C.; Johnston, C. P.; Concellón, C.; Simal, C.; Philp, D.; Smith, A. D. Angew. Chem., Int. Ed. 2009, 48, 8914
26. Uraguchi, D.; Koshimoto, K.; Miyake, S.; Ooi, T. Angew. Chem., Int. Ed. 2010, 49, 5567
27. Zhang, Z.; Xie, F.; Jia, J.; Zhang, W. J. Am. Chem. Soc. 2010, 132, 15939
28. Campbell, C. D.; Concellón, C.; Smith, A. D. Tetrahedron: Asymmetry 2011, 22, 797
29. Joannesse, C.; Johnston, C. P.; Morrill, L. C.; Woods, P. A.; Kieffer, M.; Nigst, T. A.; Mayr, H.; Lebl, T.; Philp, D.; Bragg, R. A.; Smith, A. D. Chem.-Eur. J. 2012, 18, 2398
30. De, C. K.; Mittal, N.; Seidel, D. J. Am. Chem. Soc. 2011, 133, 16802
31. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176
32. Candish, L.; Lupton, D. W. Org. Lett. 2010, 12, 4836
33. Candish, L.; Lupton, D. W. Chem. Sci 2012, 3, 380
34. Carreira, E. M. In Comprehensive Asymmetric Catalysis III; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Chapter 29.1, p 997.
35. Uraguchi, D.; Koshimoto, K.; Ooi, T. J. Am. Chem. Soc. 2008, 130, 10878
36. Uraguchi, D.; Koshimoto, K.; Sanada, C.; Ooi, T. Tetrahedron: Asymmetry 2010, 21, 1189
37. Uraguchi, D.; Koshimoto, K.; Ooi, T. Chem. Commun. 2010, 46, 300
38. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
39. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
40. Peddibhotla, S. Curr. Bioact. Compd. 2009, 5, 20
41. Wu, Y.-J. Top. Heterocycl. Chem. 2010, 26, 1
42. Russel, J. S. Top. Heterocycl. Chem 2010, 26, 397
43. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
44. Badillo, J. J.; Hanhan, N. V.; Franz, A. K. Curr. Opin. Drug Discovery 2010, 13, 758
45. Ogawa, S.; Shibata, N.; Inagaki, J.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2007, 46, 8666
46. Shen, K.; Liu, X.; Zheng, K.; Li, W.; Hu, X.; Lin, L.; Feng, X. Chem.-Eur. J. 2010, 16, 3736
47. Shen, K.; Liu, X.; Wang, W.; Wang, G.; Cao, W.; Li, W.; Hu, X.; Lin, L.; Feng, X. Chem. Sci. 2010, 1, 590
48. Pesciaioli, F.; Righi, P.; Mazzanti, A.; Gianelli, C.; Mancinelli, M.; Bartoli, G.; Bencivenni, G. Adv. Synth. Catal. 2011, 353, 2953
49. Chen, W.-B.; Wu, Z.-J.; Hu, J.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Org. Lett. 2011, 13, 2472