Highly enantioselective addition of diethylzinc to diphenylphosphinoyl imines under dual amino alcohol/ halosilane mediation

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3157-3159

  Jimeno, Ciril ^a   Reddy, K Subba ^a   Solà, Lluís ^a   Moyano, Albert ^a   Pericàs, Miquel A ^a   Riera, Antoni ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001232515     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006354c     Document Type: Article

References (22)

1. For some examples, see: (a) Stirling, D. I. In Chirality in Industry; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; John Wiley and Sons: Chichester, 1992; pp 209-222.
2. (b) Federsel, H.-J. In Chirality in Industry II; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; John Wiley and Sons: Chichester, 1997; pp 225-244.
3. For a review on the enantioselective synthesis of amines, see: Johansson, A. Contemp. Org. Synth. 1995, 2, 393-408.
4. For a recent comprehensive review, see: Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094.
5. For leading references, see: (a) Verdaguer, X.; Lange, U. E. W.; Reding, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 6784-6785.
6. (b) Verdaguer, X.; Lange, U. E. W.; Buchwald, S. L. Angew. Chem. Int. Ed. 1998, 37, 1103-1107.
7. For reviews, see: (a) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999-1004.
8. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895-1946.
9. (a) Soai, K.; Hatanaka, T.; Miyazawa, T. J. Chem. Soc., Chem. Commun. 1992, 1097-1098.
10. (b) Andersson, P. G.; Guijarro, D.; Tanner, D. Synlett 1996, 727-728.
11. (c) Andersson, P. G.; Guijarro, D.; Tanner, D. J. Org. Chem. 1997, 62, 7364-7375.
12. (d) Guijarro, D.; Pinho, P.; Andersson, P. G. J. Org. Chem. 1998, 63, 2530-2535.
13. Brandt, P.; Hedberg, C.; Lawonn, K.; Pinho, P.; Andersson, P. G. Chem. Eur. J. 1999, 5, 1692-1699.
14. Jimeno, C.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1999, 40, 777-780.
15. (a) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Heidelberg, 1999; pp 649-677.
16. (b) Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380.
17. Solà, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J. F. J. Org. Chem. 1998, 63, 7078-7082.
18. Reddy, K. S.; Sola, L.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1999, 64, 3969-3974.
19. Reddy, K. S.; Sola, L.; Moyano, A.; Pericàs, M. A.; Riera, A. Synthesis 2000, 165-176.
20. Slightly higher enantioselectivities are observed in the addition to this substrate mediated by the 2-azabornyl-3-methanol ligands developed by Andersson (see ref 6).
21. R 35.5 min) and found to be S (94% ee).
22. The addition of diethylzinc to the diphenylphosphinoyl imine of cinnamaldehyde mediated by the 4a/TIPSCl system takes place in high yield (91%) but with disappointingly low enantioselectivity (5%).