Enantioselective organocatalytic rearrangement of α-acyloxy- β-keto sulfides to α-acyloxy thioesters

Advanced Synthesis and Catalysis

Volumn 352, Issue 17, 2010, Pages 2955-2960

  Capitta, Francesca ^a   Frongia, Angelo ^a   Piras, Pier Paolo ^a   Pitzanti, Patrizia ^a   Secci, Francesco ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Cinchona alkaloids; domino reaction; enantioselectivity; organocatalysis; protonation; Pummerer reaction

Indexed keywords

EID: 78649598271     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000376     Document Type: Article

References (54)

1. P. I. Dalko, Enantioselective Organocatalysis: Reactions and Experimental Procedures, Wiley-VCH, Weinheim, 2007
2. A. Berkessel, H. Groger, Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005
3. G. Guillena, C. Najera, D. J. Ramon, Tetrahedron: Asymmetry 2007, 18, 2249
4. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232
5. Angew. Chem. Int. Ed. 2008, 47, 6138.
6. S. Iriuchijima, K. Maniwa, G.-I. Tsuchihashi, J. Am. Chem. Soc. 1975, 97, 596-599
7. G. A. Russell, G. J. Mikol, J. Am. Chem. Soc. 1966, 88, 5498-5504
8. A. Pusino, F. Soccolini, V. Rosnati, Gazz. Chim. Ital. 1984, 114, 395-398
9. T. Mimoto, K. Terashima, S. Nojima, H. Takaku, M. Nakayama, M. Shinthani, T. Yamaoka, H. Hayashi, Bioorg. Med. Chem. 2004, 12, 281-293
10. T. Suzuki, Y. Honda, K. Izawa, R. M. Williams, J. Org. Chem. 2005, 70, 7317-7323.
11. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1345-1353
12. G. Tsuchihashi, S. Iriuchijima, M. Ishibashi, Tetrahedron Lett. 1972, 13, 4605-4608.
13. I. Kuwajima, H. Iwasawa, Tetrahedron Lett. 1974, 15, 107-110
14. P. A. Grieco, C. S. Pogonowski, J. Org. Chem. 1974, 39, 732-734.
15. Enantiomerically pure α-hydroxy acids and esters are important synthetic building blocks and have found numerous applications in medicinal chemistry and organic synthesis in general:, C. M. Coppola, H. F. Schuster, α-Hydroxy Acids in Enantioselective Synthesis, Wiley-VCH, New York, 1997.
16. For reviews on enantioselective protonation, see L. Duhamel, P. Duhamel, J. C. Plaquevent, Tetrahedron: Asymmetry 2004, 15, 3653-3691
17. C. Fehr, Angew. Chem. 1996, 108, 2726-2748
18. Angew. Chem. Int. Ed. Engl. 1996, 35, 2566-2587
19. J. Eames, N. Weerasooriya, Tetrahedron: Asymmetry 2001, 12, 1-24
20. A. Yanagisawa, K. Ishihara, H. Yamamoto, Synlett 1997, 411-420
21. J. Eames, N. Weerasooriya, J. Chem. Res. Synop. 2001, 2
22. J. T. Mohr, A. Y. Hong, B. M. Stolts, Nature Chem. 2009, 1, 359-369.
23. For the formation of transient enolates through addition to ketenes, see H. Pracejus, Justus Liebigs Ann. Chem. 1960, 634, 9-22
24. C. Fehr, I. Stempf, J. Galindo, Angew. Chem. 1993, 105, 1093-1095
25. Angew. Chem. Int. Ed. Engl. 1993, 32, 1044-1046
26. S. L. Wiskur, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 6176-6177
27. B. L. Hodous, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 10006-10007. For the formation of transient enolates by conjugate addition, see
28. H. Pracejus, F.-W. Wilcke, K. Hanemann, J. Prakt. Chem. 1977, 319, 219-229
29. P. M. T. Ferreira, H. L. S. Maia, L. S. Montero, J. Sacramento, J. Chem. Soc. Perkin Trans. 1 2001, 3167-3173
30. P. M. T. Ferreira, H. L. S. Maia, L. S. Montero, J. Sacramento, J. Sebastiao, J. Chem. Soc. Perkin Trans. 1 2000, 3317-3324
31. Y. N. Belokon, S. Harutyunyan, E. V. Vorontsov, A. S. Peregudov, V. N. Chrustalev, K. A. Kochetkov, D. Pripadchev, A. S. Sagyan, A. K. Beck, D. Seebach, ARKIVOC 2004, 132-150
32. B.-J. Li, L. Jiang, M. Liu, Y.-C. Chen, L.-S. Ding, Y. Wu, Synlett 2005, 603-606
33. D. Leow, S. Lin, S. K. Chittimalla, X. Fu, C.-H. Tan, Angew. Chem. 2008, 120, 5723-5727
34. Angew. Chem. Int. Ed. 2008, 47, 5641-5645
35. Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2006, 128, 3928-3930
36. B. Wang, F. Wu, Y. Wang, X. Liu, L. Deng, J. Am. Chem. Soc. 2007, 129, 768-769. Enantioselective decarboxylation/re-protonation of malonate derivatives was reported previously by means of cinchona alkaloids, and represent a further example of metal-free enantioselective protonation, see
37. H. Brunner, P. Schmidt, Eur. J. Org. Chem. 2000, 2119-2133
38. L. M. A. Roger, J. Rouden, L. Lecomte, M. C. Lasne, Tetrahedron Lett. 2003, 44, 3047-3050
39. T. Seitz, J. Baudoux, H. Bekolo, D. Cahard, J. C. Plaquevent, M. C. Lasne, J. Rouden, Tetrahedron 2006, 62, 6155-6165. For the formation of transient enolates through Hénin/Muzart Norrish type II fragmentation, see
40. F. Hénin, J. Muzart, J.-P. Pete, A. M'boungou-M'passi, H. Rau, Angew. Chem. 1991, 103, 460-462
41. Angew. Chem. Int. Ed. Engl. 1991, 30, 416-418.
42. For reviews on chiral Cinchona alkaloid catalysts, see
43. C. E. Song, Cinchona Alkaloids in Synthesis & Catalysis, Wiley-VCH, Weinheim, 2009
44. S. J. Connon, Chem. Commun. 2008, 2499-2510
45. T. Marcelli, J. H. vanMaarseveen, H. Hiemstra, Angew. Chem. 2006, 118, 7658-7666
46. Angew. Chem. Int. Ed. 2006, 45, 7496-7504
47. S.-K. Tian, Y. G. Chen, J. F. Hang, L. Tang, P. McDaid, L. Deng, Acc. Chem. Res. 2004, 37, 621-631
48. Y. G. Chen, P. McDaid, L. Deng, Chem. Rev. 2003, 103, 2965-2984.
49. It is noteworthy that both quinine II and (-)-N-methylephedrine IV have the same configuration (1R,2S) of the amino alcohol moiety.
50. [2c]).
51. B. Larissegger-Schnell, S. M. Glueck, W. Kroutil, K. Faber, Tetrahedron 2006, 62, 2912-2916
52. G. Iwasaki, R. Kimura, N. Numao, K. Kondo, Chem. Pharm. Bull. 1989, 37, 280-283.
53. A. Tasaka, N. Tamura, Y. Matsushita, K. Teranishi, R. Hayashi, K. Okonogi, K. Itoh, Chem. Pharm. Bull. 1993, 41, 1035-1042.
54. S. Katayama, N. Ae, T. Kodo, S. Masumoto, S. Hourai, C. Tamamura, H. Tanaka, R. Nagata, J. Med. Chem. 2003, 46, 691-701.