Asymmetric synthesis of α-acyl-γ-butyrolactones possessing all-carbon quaternary stereocenters by phase-transfer-catalyzed alkylation

Advanced Synthesis and Catalysis

Volumn 348, Issue 12-13, 2006, Pages 1539-1542

  Ooi, Takashi ^a   Miki, Takashi ^a   Fukumoto, Kazuhiro ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

acyl butyrolactones; Chiral quaternary ammonium bromide; Organic catalysis; Phase transfer alkylation; Quaternary carbon centers

Indexed keywords

EID: 33748283341     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606064     Document Type: Article

References (34)

1. For recent reviews on catalytic asymmetric synthesis of quaternary carbon centers: a) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402;
2. Angew. Chem. Int. Ed. 1998, 37, 388;
3. b) J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725;
4. Angew. Chem. Int. Ed. 2001, 40, 4591;
5. c) I. Denissova, L. Barriault, Tetrahedron 2003, 59, 10105;
6. d) C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363;
7. e) J. Christoffers, A. Baro, Adv. Synth. Catal. 2005, 347, 1473.
8. T. Ooi, T. Miki, M. Taniguchi, M. Shiraishi, M. Takeuchi, K. Maruoka, Angew. Chem. 2003, 115, 4111;
9. Angew. Chem. Int. Ed. 2003, 42, 3796;
10. see also: T. Ooi, T. Miki, K. Maruoka, Org. Lett. 2005, 7, 191.
11. For recent examples of catalytic asymmetric synthesis of α-quaternary keto lactones, see: a) H. Li, Y. Wang, L. Tang, F. Wu, X. Liu, C. Guo, B. M. Foxman, L. Deng, Angew. Chem. 2005, 117, 107;
12. Angew. Chem. Int. Ed. 2005, 44, 105;
13. b) A. H. Mermerian, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 5604.
14. a) T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka, Angew. Chem. 2002, 114, 4724;
15. Angew. Chem. Int. Ed. 2002, 41, 4542;
16. b) T. Ooi, M. Kameda, M. Taniguchi, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 9685;
17. c) T. Ooi, S. Fujioka, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 11790;
18. d) T. Ooi, M. Takeuchi, D. Kato, Y. Uematsu, E. Tayama, D. Sakai, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 5073.
19. [13] eventually confirming the absolute configuration of the adjacent α-quaternary stereocenter of 6 to be S. (Diagram Presented)
20. Unfortunately, the reaction with less reactive alkyl halides such as methyl iodide proceeded very sluggishly under similar conditions.
21. a) G. I. Georg, X. Guan, J. Kant, Tetrahedron Lett. 1988, 29, 403;
22. b) M. Moreno-Mañas, E. Trepat, R. M. Sebastian, A. Vallribera, Tetrahedron: Asymmetry 1999, 10, 4211;
23. c) M. Tanaka, M. Oba, K. Tamai, H. Suemune, J. Org. Chem. 2001, 66, 2667;
24. d) H.-J. Cristau, X. Marat, J.-P. Vors, J.-L. Pirat, Tetrahedron Lett. 2003, 44, 3179;
25. e) M. Tanaka, S. Nishimura, M. Oba, Y. Demizu, M. Kurihara, H. Suemune, Chem. Eur. J. 2003, 9, 3082.
26. M. L. Pedersen, D. B. Berkowitz, J. Org. Chem. 1993, 58, 6966.
27. For similar acylation of γ-butyrolactone, see, for example: a) M. M. Campbell, J. L. Fox, M. Sainsbury, Y. Liu Tetrahedron 1989, 45, 4551;
28. b) P. M. Pihko, A. Pohjakallio, Synlett 2004, 2115.
29. S. Takei, Y. Kawano, Tetrahedron Lett. 1975, 16, 4389.
30. C. R. Sarko, I. C. Guch, M. DiMare, J. Org. Chem. 1994, 59, 705.
31. For a similar stereochemical assignment of β-hydroxy lactones, see: a) M. Takeshita, H. Yanagihara, S. Yoshida, Heterocycles 1992, 33, 489;
32. b) M. Abe, M. Ikeda, M. Nojima, J. Chem. Soc., Perkin Trans. 1 1998, 3261;
33. c) L. H. P. Teixeira, M. C. B. V. de Souza, M. C. K. V. Ramos, F. R. de Aquino Neto, E. J. Barreiro, C. A. M. Fraga, Synth. Commun. 2002, 32, 505.
34. I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092.