Enantioselective aza-Henry reactions assisted by ZnII and N-methylephedrine

Angewandte Chemie - International Edition

Volumn 45, Issue 1, 2005, Pages 117-120

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   Halder, Rajkumar ^a   Laso, Antonio ^a   López, Rosa ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Amines; Asymmetric catalysis; Enantioselectivity; Nitro compounds

Indexed keywords

AMINES; CATALYSIS; REACTION KINETICS;

ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; NITRO COMPOUNDS;

STEREOCHEMISTRY;

EID: 29344439102     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502674     Document Type: Article

References (38)

1. For recent advances on this reaction, see: B. Westermann, Angew. Chem. 2003, 115, 161-163;
2. Angew. Chem. Int. Ed. 2003, 42, 151-153.
3. For a review on 1,2-diamines, see: D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772;
4. Angew. Chem. Int. Ed. 1998, 37, 2580-2627.
5. See, for instance: P. H. O'Brien, D. R. Sliskovic, C. J. Blankley, B. Roth, M. W. Wilson, K. L. Hamelehle, B. R. Krause, R. L. Stanfield, J. Med. Chem. 1994, 37, 1810-1822.
6. For reviews, see: a) H. W. Pinnick, Org. React. 1990, 38, 655-792;
7. b) R. Ballini, M. Petrini, Tetrahedron 2004, 60, 1017-1047.
8. For the application of this approach to the synthesis of optically active α-amino acids; see: c) E. Foresti, G. Palmieri, M. Petrini, R. Profeta, Org. Biomol. Chem. 2003, 1, 4275-4281.
9. For non-asymmetric aza-Henry reactions, see: a) J. C. Anderson, A. J. Blake, G. P. Howell, C. W. Ilson, J. Org. Chem. 2005, 70, 549-555;
10. b) L. Bernardi, B. F. Bonini, E. Capitó, G. Dessole, M. Comes-Franchini, M. Fochi, A. Ricci, J. Org. Chem. 2004, 69, 8168-8171.
11. a) K. Yamada, S. J. Harwood, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 3713-3715;
12. Angew. Chem. Int. Ed. 1999, 38, 3504-3506;
13. b) K. Yamada, G. Moll, M. Shibasaki, Synlett 2001, 980-982.
14. a) K. R. Knudsen, T. Risgaard, N. Nishiwaki, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 2001, 123, 5843-5844.
15. For latter versions using unmodified nitro compounds, see: b) N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080-3083;
16. Angew. Chem. Int. Ed. 2001, 40, 2992-2995;
17. c) K. R. Knudsen, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 1362-1364.
18. II/ tBOX catalyst with generally good diastereo- and enantioselectivities has been recently published, see: J. C. Anderson, G. P. Howell, R. M. Lawrence, C. S. Wilson, J. Org. Chem. 2005, 70, 5665-5670.
19. a) B. M. Nugent, R. A. Poder, J. N. Johnston, J. Am. Chem. Soc. 2004, 126, 3418-3419;
20. b) T. Okino, S. Nakamura, T. Furukawa, Y. Takemoto, Org. Lett. 2004, 6, 625-627;
21. c) T. P. Yoon, E. N. Jacobsen, Angew. Chem. 2005, 117, 470-472;
22. Angew. Chem. Int. Ed. 2005, 44, 466-468.
23. C. Palomo, M. Oiarbide, A. Laso, Angew. Chem. 2005, 117, 3949-3952;
24. Angew. Chem. Int. Ed. 2005, 44, 3881-3884.
25. For recent reviews on cooperative activation of nucleophiles (or pronucleophiles) and electrophiles, see: a) J.-A. Ma, D. Cahard, Angew. Chem. 2004, 116, 4666-4683;
26. Angew. Chem. Int. Ed. 2004, 43, 4566-4583;
27. b) S. Kanemasa, K. Ito, Eur. J. Org. Chem. 2004, 4741-4753.
28. For other recent uses of N-methylephedrine, such as the addition of acetylides to aldehydes, see: a) N. K. Anand, E. M. Carreira, J. Am. Chem. Soc. 2001, 123, 9687-9688;
29. b) D. E. Frautz, R. Fässler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806-1807;
30. for imino-Reformatsky reaction, see: c) P. G. Cozzi, E. Rivalta, Angew. Chem. 2005, 117, 3666-3669;
31. Angew. Chem. Int. Ed. 2005, 44, 3600-3603.
32. Benzaldehyde-derived imines from p-anisidine and benzylamine did not react under the conditions described. These kind of imines have been shown to be active against preformed silyl nitronates in the presence of a Lewis acid. See, for instance, reference [8].
33. Apparently, heteroaromatic N-Boc-protected imines are less-suitable substrates for the reaction. For instance, the aza-Henry adduct from the furfuraldehyde N-Boc imine derivative was obtained in 96% yield and with 66% ee.
34. P. H. O'Brien, D. R. Sliskovic, C. J. Blankley, B. Roth, M. W. Wilson, K. L. Hamelehle, B. R. Krause, R. L. Stanfield, J. Med. Chem. 1994, 37, 1810-1822.
35. a) C. Matt, A. Wagner, C. Mioskowski, J. Org. Chem. 1997, 62, 234-235.
36. For the application of this method to the synthesis of α-hydroxy acids from β-nitro alcohols, see: b) B. M. Trost, V. S. C. Yeh, Angew. Chem. 2002, 114, 889-891;
37. Angew. Chem. Int. Ed. 2002, 41, 861-863.
38. 4) led to partially racemized 11a (65% yield, 70% ee).