Highly diastereo- and enantioselective formal conjugate addition of nitroalkanes to nitroalkenes by chiral ammonium bifluoride catalysis

Angewandte Chemie - International Edition

Volumn 45, Issue 45, 2006, Pages 7606-7608

  Ooi, Takashi ^a,b   Takada, Saki ^a   Doda, Kanae ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

1,3 dinitro compounds; Asymmetric catalysis; C C coupling; Conjugate addition; Homogeneous catalysis

Indexed keywords

ADDITION REACTIONS; AMMONIUM COMPOUNDS; CATALYSIS; CATALYST SELECTIVITY; CHEMICAL BONDS; STEREOCHEMISTRY;

ASYMMETRIC CATALYSIS; C-C COUPLING; HOMOGENEOUS CATALYSIS; NITROALKENES;

PARAFFINS;

EID: 33845202019     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602787     Document Type: Article

References (27)

1. a) N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001, chaps. 4 and 6;
2. for a recent example of facile transformations of optically active organonitro compounds, see: b) C. Czekelius, E. M. Carreira, Angew. Chem. 2005, 117, 618;
3. Angew. Chem. Int. Ed. 2005, 44, 612.
4. a) O. M. Berner, L. Tedeschi, D. Enders, Eur. J. Org. Chem. 2002, 1877;
5. for recent examples, see: b) D. J. Dixon, R. D. Richardson, Synlett 2006, 81;
6. c) S. B. Tsogoeva, S. Wei, Chem. Commun. 2006, 1451;
7. d) M. Terada, H. Ube, Y. Yaguchi, J. Am. Chem. Soc. 2006, 128, 1454;
8. e) P. J. Nichols, J. A. DeMattei, B. R. Barnett, N. A. LeFur, T.-H. Chuang, A. D. Piscopio, K. Koch, Org. Lett. 2006, 8, 1495;
9. f) H. Huang, E. N. Jacobsen, J. Am. Chem. Soc. 2006, 128, 7170, and references therein.
10. a) M. Yamaguchi in Comprehensive Asymmetric Catalysis, Vol. 3 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, chap. 31.2;
11. b) M. Yamaguchi in Comprehensive Asymmetric Catalysis Supplement 1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 2004, p. 151;
12. c) R. Ballini, G. Bosica, D. Fiorini, A. Palmieri, M. Petrini, Chem. Rev. 2005, 105, 933.
13. For a few examples of non-stereoselective reactions, see: a) M. D. Alcántara, F. C. Escribano, A. Gómez-Sánchez, M. J. Diánez, M. D. Estrada, A. López-Castro, S. Pérez-Garrido, Synthesis 1996, 64;
14. b) R. Ballini, G. Bosica, D. Fiorini, A. Palmieri, Synthesis 2004, 1938.
15. S.-F. Lu, D.-M. Du, J. Xu, S.-W. Zhang, J. Am. Chem. Soc. 2006, 128, 7418.
16. For an account of chiral ammonium fluoride catalysis, see: T. Ooi, K. Maruoka, Acc. Chem. Res. 2004, 37, 526.
17. a) T. Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 2054;
18. b) T. Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 9022;
19. c) T. Ooi, K. Doda, S. Takada, K. Maruoka, Tetrahedron Lett. 2006, 47, 145.
20. 2O, approximately 60% of deuterium incorporation was observed at the C1 methylene center of syn-7a, thereby suggesting the intervention of a silyl nitronate intermediate of type 10. We assume that the low deuterium incorporation could be ascribed to the high susceptibility of the silyl nitronate, generated in situ, to protonation from a small amount of water or methanol.
21. Although 1.2 equiv of silyl nitronate 6 seemed to be sufficient, we decided to use 2 equiv of 6 at 0.04 M substrate concentration for further investigations to constantly attain excellent yields.
22. For selected examples, see: a) C. F. Bigge, J.-P. Wu, J. T. Drummond, Bioorg. Med. Chem. Lett. 1992, 2, 207;
23. b) G. H. P. Roos, A. R. Donovan, Tetrahedron: Asymmetry 1999, 10, 991;
24. c) S. E. Denmark, J.-H. Kim, Can. J. Chem. 2000, 78, 673;
25. d) M. M. Kabat, Tetrahedron Lett. 2001, 42, 7521;
26. e) F. Cohen, L. E. Overman, J. Am. Chem. Soc. 2001, 123, 10782.
27. The ee value of syn-11 was confirmed by HPLC analysis after derivatization to the corresponding cyclic thiourea. See the Supporting Information.