Brønsted acid catalyzed asymmetric aldol reaction: A complementary approach to enamine catalysis

Organic Letters

Volumn 12, Issue 16, 2010, Pages 3582-3585

  Pousse, Guillaume ^a   Cavelier, Fabien Le ^a   Humphreys, Luke ^b   Rouden, Jacques ^a   Blanchet, Jérôme ^a  

^a CNRS   (France)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDOAMANITIN; AMANITIN; KETONE; PHOSPHORIC ACID;

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

AMANITINS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MOLECULAR STRUCTURE; PHOSPHORIC ACIDS; STEREOISOMERISM;

EID: 77955668363     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101176j     Document Type: Article

References (41)

1. Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, 2004.
2. Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120
3. Geary, L. M.; Hultin, P. G. Tetrahedron: Asymmetry 2009, 20, 131-173
4. Zlotin, S. G.; Kucherenko, A. S.; Beletskaya, I. P. Russ. Chem. Rev. 2009, 78, 737-784
5. Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615-1621
6. Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. 1971, 10, 496-497
7. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569
8. Trost, B. M.; Shin, S.; Sclafani, J. A. J. Am. Chem. Soc. 2005, 127, 8602-8603
9. Mizuno, M.; Inoue, H.; Naito, T.; Zhou, L.; Nishiyama, H. Chem.-Eur. J. 2009, 15, 8985-8988
10. Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497-2500
11. Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169-2178
12. Akiyama, T. Chem. Rev. 2007, 107, 5744-5758
13. Terada, M. Chem. Commun. 2008, 35, 4097-4112
14. Terada, M. Synthesis 2010, 1929-1982
15. Xu, S.; Wang, Z.; Wang, X.; Zhang, X.; Ding, K. Angew. Chem., Int. Ed. 2008, 47, 2840-2843
16. Rueping, M.; Nachtsheim, B. J.; Moreth, S. A.; Bolte, M. Angew. Chem., Int. Ed. 2008, 47, 593-596
17. Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C. J. Am. Chem. Soc. 2007, 129, 12084-12085
18. Rueping, M.; Ieawsuwan, W.; Antonchick, A. P.; Nachtsheim, B. J. Angew. Chem., Int. Ed. 2007, 46, 2097-2100
19. Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 9626-9627
20. Rueping, M.; Theissmann, T.; Kuenkel, A.; Koenigs, R. M. Angew. Chem., Int. Ed. 2008, 47, 6798-6801
21. Akiyama, T.; Katoh, T.; Mori, K. Angew. Chem., Int. Ed. 2009, 48, 4226-4228
22. Lu, M.; Zhu, D.; Lu, Y.; Zeng, X.; Tan, B.; Xu, Z.; Zhong, G. J. Am. Chem. Soc. 2009, 131, 4562-4563
23. Gu, Q.; Rong, Z.-Q.; Zheng, C.; You, S.-L. J. Am. Chem. Soc. 2010, 132, 4056-4057
24. Sun, F.-L.; Zeng, M.; Gu, Q.; You, S.-L. Chem.-Eur. J. 2009, 15, 8709-8712
25. For previous asymetric Mukaiyama aldol reactions catalyzed with chiral Brønsted acids, see
26. Cheon, C. H.; Yamamoto, H. Org. Lett. 2010, 12, 2476-2479
27. García-García, P.; Lay, F.; García-García, P.; Rabalakos, C.; List, B. Angew. Chem., Int. Ed. 2009, 48, 4363-4366
28. McGilvra, J. D.; Unni, A. K.; Modi, K.; Rawal, V. H. Angew. Chem., Int. Ed. 2006, 45, 6130-6133
29. Gondi, V. B.; Hagihara, K.; Rawal, V. H. Angew. Chem., Int. Ed. 2009, 48, 776-779
30. Zhuang, W.; Poulsen, T. B.; Jørgensen, K. A. Org Biomol. Chem. 2005, 3, 3284-3289
31. For previous activation of ethyl glyoxylate by chiral phosphoric acids, see: Terada, M.; Soga, K.; Momiyama, N. Angew. Chem., Int. Ed. 2008, 47, 4122-4125
32. Momiyama, N.; Tabuse, H.; Terada, M. J. Am. Chem. Soc. 2009, 131, 12889-12890
33. Other electrophiles were tested (2-methylpropanal, 1-butanal, chloral, 2-and 3-pyridine carboxaldehyde, benzaldehyde, phenyl glyoxal), and only traces of product were detected. Ethyl trifluoropyruvate delivered 42% yield.
34. Pousse, G.; Devineau, A.; Dalla, V.; Humphreys, L.; Lasne, M.-C.; Rouden, J.; Blanchet, J. Tetrahedron 2009, 65, 10617-10622
35. 2) was prepared and the obtained selectivities were identical to those of 3c (at 0 °C: 75% yield, 80:20 dr, 89:11 er).
36. See the Supporting Information for more details.
37. Only in rare cases were organocatalysts reported to be general syn-selective aldol catalysts.
38. Luo, S.; Xu, H.; Li, J.; Zhang, L.; Cheng, J.-P. J. Am. Chem. Soc. 2007, 129, 3074-3075
39. Kano, T.; Yamaguchi, Y.; Tanaka, Y.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 7606-7608. α-Hydroxy ketones are known to deliver syn selectivity;
40. see: Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F., III. J. Am. Chem. Soc. 2007, 129, 288-289
41. Palyam, N.; Majewski, M. J. Org. Chem. 2009, 74, 4390-4392