Organocatalytic stereoselective direct aldol reaction of trifluoroethyl thioesters

Advanced Synthesis and Catalysis

Volumn 353, Issue 6, 2011, Pages 848-854

  Rossi, Sergio ^a   Benaglia, Maurizio ^a   Cozzi, Franco ^a   Genoni, Andrea ^a   Benincori, Tiziana ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

aldol reaction; organocatalysis; phosphine oxides; tetrachlorosilane; thioesters

Indexed keywords

EID: 79955378501     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100122     Document Type: Article

References (32)

1. A. Berkessel, H. Groger, (Eds.), Asymmetric Organic Catalysis, Wiley-VCH, Weinheim, 2005.
2. F. G. Bordwell, H. E. Fried, J. Org. Chem. 1991, 56, 4218.
3. A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716
4. A. Dondoni, A. Massi, Angew. Chem. Int. Ed. 2008, 47, 4638.
5. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232
6. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. Int. Ed. 2008, 47, 6138.
7. S. Orlandi, M. Benaglia, F. Cozzi, Tetrahedron Lett. 2004, 45, 1747
8. D. Magdziak, G. Lalic, H. M. Lee, K. C. Fortner, A. D. Aloise, M. D. Shair, J. Am. Chem. Soc. 2005, 127, 7284.
9. A. Ricci, D. Pettersen, L. Bernardi, F. Fini, M. Fochi, R. Perez Herrera, V. Sgarzani, Adv. Synth. Catal. 2007, 349, 1037.
10. J. Lubkoll, H. Wennemers, Angew. Chem. 2007, 119, 6965
11. J. Lubkoll, H. Wennemers, Angew. Chem. Int. Ed. 2007, 46, 6841.
12. C. Cassani, L. Bernardi, F. Fini, A. Ricci, Angew. Chem. 2009, 121, 5804
13. C. Cassani, L. Bernardi, F. Fini, A. Ricci, Angew. Chem. Int. Ed. 2009, 48, 5694.
14. D. A. Alonso, S. Kitagaki, N. Utsumi, C. F. Barbas III, Angew. Chem. 2008, 120, 4664
15. D. A. Alonso, S. Kitagaki, N. Utsumi, C. F. Barbas III, Angew. Chem. Int. Ed. 2008, 47, 4588.
16. N. Utsumi, S. Kitagaki, C. F. Barbas III, Org. Lett. 2008, 10, 3405.
17. For a review on Lewis base-catalyzed reactions see:, S. E. Denmark, G. L. Beutner, Angew. Chem. 2008, 120, 1584
18. S. E. Denmark, G. L. Beutner, Angew. Chem. Int. Ed. 2008, 47, 1560.
19. S. E. Denmark, T. Wynn, G. L. Beutner, J. Am. Chem. Soc. 2002, 124, 13405.
20. For a recent review on hypervalent silicates-mediated reactions see:, M. Benaglia, S. Guizzetti, L. Pignataro, Coord. Chem. Rev. 2008, 252, 492.
21. For a recent review article dedicated to the use of chiral phosphine oxides in organocatalysis see:, S. Rossi, M. Benaglia, Org. Biomol. Chem. 2010, 8, 3824.
22. S. Kotani, Y. Shimoda, M. Sugiura, M. Nakajima, Tetrahedron Lett. 2009, 50, 4602.
23. S. Rossi, M. Benaglia, A. Genoni, T. Benincori, G. Celentano, Tetrahedron 2010, in press, doi: 10.1016/j.tet.2010.11.009.
24. [19].
25. S. Hadachi, T. Harada, Org. Lett. 2008, 10, 4999.
26. F. Fringuelli, O. Piermatti, F. Pizzo, J. Org. Chem. 1995, 60, 7006.
27. V. Simonini, M. Benaglia, T. Benincori, Adv. Synth. Catal. 2008, 350, 561.
28. [11,13]. See also, S. E. Denmark, Y. Fan, M. D. Eastgate, J. Org. Chem. 2005, 70, 5235.
29. 31P NMR studies in the field see:, S. E. Denmark, B. M. Eklov, Chem. Eur. J. 2008, 14, 234-239.
30. It must be noted that on simply mixing tetra-Me- BITIOPO with HCl a shift in the P signal to 31.7 ppm (instead of 34.8) was detected and that no change was observed after addition of DIPEA. Under the present analysis conditions the in situ formation of a silyl ketene thioacetal in solution was not clearly observed.
31. C. Gennari, M. G. Beretta, A. Bernardi, G. Moro, C. Scolastico, R. Todeschini, Tetrahedron 1986, 42, 893.
32. D. A. Evans, J. V. Nelson, E. Vogel, T. R. Taber, J. Am. Chem. Soc. 1981, 103, 3099.