Catalytic asymmetric conjugate addition of dialkylzinc reagents to α,β-unsaturated sulfones

Organic and Biomolecular Chemistry

Volumn 8, Issue 1, 2010, Pages 47-49

  Bos, Pieter H ^a   Maciá, Beatriz ^a   Angeles Fernandez Ibanez M ^a   Minnaard, Adriaan J ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CONJUGATE ADDITION; CONJUGATE ADDITION; DIALKYLZINC REAGENTS; EFFICIENT METHOD; ENANTIOSELECTIVE; MONODENTATES; PHOSPHORAMIDITE LIGANDS;

EID: 76849085423     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b917269f     Document Type: Article

References (32)

1. (a) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis; Tetrahedron Organic Chemistry Series 9, Pergamon Press, Oxford, U.K., 1992;
2. (b) B. E. Rossiter and N. M. Swingle, Chem. Rev., 1992, 92, 771-806.
3. (a) For reviews, see: K. Tomioka and Y. Nagaoka, in Comprehensive Asymmetric Catalysis, ed. E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, New York, 1999, Vol.3, pp. 1105-1120;
4. (b) B. L. Feringa, Acc Chem. Res., 2000, 33, 346-353;
5. (c) N. Krause and A. Hoffmann-Röder, Synthesis, 2001,171-196;
6. (d) B. L. Feringa, R. Naasz, R. Imbos and L. A. Arnold, in Modem Organocopper Chemistry, ed. N. Krause, VCH, Weinheim, Germany, 2002, pp. 224-258;
7. (e) A. Alexakis and C. Benhaim, Eur. J. Org. Chem., 2002, 3221-3236;
8. (f) T. Hayashi and K. Yamasaki, Chem. Rev.,2003, 103, 2829-2844;
9. (g) S. Woodward, Angew. Chem., Int. Ed, 2005, 44, 5560-5562;
10. (h) F. Lopez, A. J. Minnaard and B. L. Feringa, in The Chemistry of Organomagnesium Compounds, ed. Z. Rappoport, I. Marek, Wiley, Chichester, U. K., 2008, Part 2, Chapter 17;
11. (i) S. R. Harutyunyan, T. den Hartog, K. Geurts, A. J. Minnaard and B. L. Feringa, Chem. Rev., 2008, 108, 2824-2852.
12. (a) E. N. Prilezhaeva, Russ. Chem. Rev., 2000, 69, 367;
13. (b) S. E. Kelly, in Comprehensive Organic Synthesis, ed. B. M. Trost, I. Flemming, Pergamon Press, Oxford, 1991, Vol.1, pp. 792;
14. (c) B. M. Trost, Bull. Chem. Soc. Jpn., 1988, 61, 107;
15. (d) N. S. Simpkins, Sulphones in Organic Synthesis; Tetrahedron Organic Chemistry Series 10, Pergamon Press, Oxford, U.K., 1993.
16. T. Llamas, R. G. Arrayás and J. C. Carretero, Angew. Chem., Int. Ed., 2007, 46, 3329-3332.
17. J.-N Desrosiers and A. B. Charette, Angew. Chem., Int. Ed., 2007, 46, 5955-5957.
18. (a)P. Mauleónand J. C. Carretero, Org. Lett.,2004, 6, 3195-3198;
19. (b)P. Mauleón and J. C. Carretero, Chem. Commun., 2005, 4961-4963;
20. (c) P. Mauleón, I. Alonso, M. R. Rivero and J. C. Carretero, J. Org. Chem., 2007, 72, 9924-9935.
21. J.-N. Desrosiers, W. S. Bechara and A. B. Charette, Org. Lett., 2008, 10, 2315-2318.
22. P. H. Bos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2008, 10, 4219-4222.
23. (a) B. L. Feringa, Acc Chem. Res., 2000, 33, 346-353;
24. (b) A. J. Minnaard, B. L. Feringa, L. Lefort and J. G. de Vries, Acc Chem. Res., 2007, 40, 1267;
25. (c) J. G. de Vries and L. Lefort, in Handbook of Homogenous Hydrogénation, ed. J. G. De Vries, C. J. Elsevier, WileyVCH Verlag, Weinheim, Germany, 2007, pp. 1245-1278;
26. (d) L. Lefort and J. G. de Vries, in Phosphorus Ligands in Asymmetric Catalysis, ed. A. Börmer, Wiley-VCH Verlag, Weinheim, Germany, 2008, pp. 1348-1376;
27. (e) R. B. C. Jagt, P. Y. Toullec, E. P. Schudde, J. G. de Vries, B. L. Feringa and A. J. Minnaard, J. Comb. Chem., 2007, 9, 407.
28. (a) A. H. M. de Vries, A. Meetsma and B. L. Feringa, Angew. Chem., Int. Ed Engl, 1996, 35, 2374;
29. (b) B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl, 1997, 36, 2620;
30. (c) A. Alexakis, D. Polet, S. Rosset and S. March, J. Org. Chem.,2004, 69, 5660;
31. (d) T. Jerphagnon, M. G. Pizzuti, A. J. Minnaard and B. L. Feringa, Chem. Soc. Rev., 2009, 38, 1039-1075.
32. This dependence is in contrast to that reported for the asymmetric conjugate addition of Grignard reagents to α,β-unsaturated sulfones where the nature of the counterion hardly had an effect on conversion and enantioselectivity, see ref. 8.