Phase-transfer catalyzed asymmetric conjugate additions of β-ketoesters to acetylenic ketones

Organic Process Research and Development

Volumn 14, Issue 3, 2010, Pages 684-686

  Lan, Quan ^a   Wang, Xisheng ^a   Shirakawa, Seiji ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77952923651     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op100014v     Document Type: Article

References (44)

1. For representative reviews on quaternary stereocenter, see: Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388
2. Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105
3. Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363
4. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Christoffers, J.; Baro, A., Eds.; Wiley-VCH: Weinheim, 2005.
5. Bella, M.; Gasperi, T. Synthesis 2009, 1583
6. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis I-III; Springer: Berlin, 1999.
7. Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; Wiley-VCH: New York, 2000.
8. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis, Suppl. 1; Springer: Berlin, 2004.
9. For examples of asymmetric conjugate addition under the influence of chiral phase-transfer catalyst, see: Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347
10. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299
11. Arai, S.; Tsuji, R.; Nishida, A. Tetrahedron Lett. 2002, 43, 9535
12. Ohshima, T.; Shibuguchi, T.; Fukuta, Y.; Shibasaki, M. Tetrahedron 2004, 60, 7743
13. Ooi, T.; Ohara, D.; Fukumoto, K.; Maruoka, K. Org. Lett. 2005, 7, 3195
14. Kano, T.; Kumano, T.; Maruoka, K. Org. Lett. 2009, 11, 2023
15. Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 5672
16. For representative reviews on asymmetric phase-transfer catalysis, see: Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Blackie Academic & Professional: London, 1997; Chapter 14, p 462.
17. Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583
18. Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vögtle, F.; Stoddart, J. F.; Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p. 123.
19. O'Donnell, M. J. In Catalytic Asymmetric Syntheses, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 10, p 727.
20. O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3
21. Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013
22. O'Donnell, M. J. Acc. Chem. Res. 2004, 37, 506
23. Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518
24. Vachon, J.; Lacour, J. Chimia 2006, 60, 266
25. Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 4222
26. Ooi, T.; Maruoka, K. Aldrichimica Acta 2007, 40, 77
27. Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656
28. Maruoka, K. Org. Process Res. Dev. 2008, 12, 679
29. Maruoka, K., Ed. Asymmetric Phase Transfer Catalysis; Wiley-VCH: Weinheim, 2008.
30. Wang, X.; Kitamura, M.; Maruoka, K. J. Am. Chem. Soc. 2007, 129, 1038
31. Lan, Q.; Wang, X.; Maruoka, K. Tetrahedron Lett. 2007, 48, 4675
32. Kitamura, M.; Shirakawa, S.; Maruoka, K. Angew. Chem., Int. Ed. 2005, 44, 1549
33. Kitamura, M.; Shirakawa, S.; Arimura, Y.; Wang, X.; Maruoka, K. Chem. Asian J. 2008, 3, 11702
34. Wang, Y.-G.; Kumano, T.; Kano, T.; Maruoka, K. Org. Lett. 2009, 11, 2027
35. Hashimoto, T.; Sakata, K.; Maruoka, K. Angew. Chem., Int. Ed. 2009, 48, 5014
36. He, R.; Shirakawa, S.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 16620
37. Wang, X.; Lan, Q.; Shirakawa, S.; Maruoka, K. Chem. Commun. 2010, 46, 321
38. Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240
39. Hamashima, Y.; Hotta, D.; Umebayashi, N.; Tsuchiya, Y.; Suzuki, T.; Sodeoka, M. Adv. Synth. Catal. 2005, 347, 1576
40. Acyclic β-keto esters as nucleophiles showed moderate reactivity and enantioselectivity (∼40% ee).
41. The Z isomer of compound 4ac could isomerize to the corresponding E isomer without loss of enantioselectivity, see: Poulsen, T. B.; Bernardi, L.; Bell, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 6551
42. Asymmetric phase-transfer reactions on a large scale, see: Patterson, D. E.; Xie, S.; Jones, L. A.; Osterhout, M. H.; Henry, C. G.; Roper, T. D. Org. Process Res. Dev. 2007, 11, 624
43. Wang, Y.-G.; Maruoka, K. Org. Process Res. Dev. 2007, 11, 628
44. Scott, J. P.; Ashwood, M. S.; Brands, K. M. J.; Brewer, S. E.; Cowden, C. J.; Dolling, U.-H.; Emerson, K. M.; Gibb, A. D.; Goodyear, A.; Oliver, S. F.; Stewart, G. W.; Wallace, D. J. Org. Process Res. Dev. 2008, 12, 723