N-Benzyl-l-prolinol: an efficient catalyst for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines

Tetrahedron Asymmetry

Volumn 18, Issue 7, 2007, Pages 896-899

  Almansa, Raquel ^a   Guijarro, David ^a   Yus, Miguel ^a  

^a Departamento de Química Orgánica   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BETA AMINOALCOHOL; IMINE; N (DIPHENYLPHOSPHINOYL)IMINE DERIVATIVE; N BENZYLPROLINOL; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REACTION TIME; ROOM TEMPERATURE;

EID: 34247579164     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.03.026     Document Type: Article

References (49)

1. Jacques J., Collet A., and Wilen S.H. Enantiomers, Racemates and Resolution (1981), John Wiley & Sons, New York
2. Moser H., Rihs G., and Santer H. Z. Naturforsch. 376 (1982) 451-462
3. Whitesell J.K. Chem. Rev. 89 (1989) 1581-1590
4. Volkmann R.A. In: Schreiber S.L. (Ed). Comprehensive Organic Synthesis Vol. 1 (1991), Pergamon Press, Oxford Chapter 1.12
5. Kleinman E.F., and Volkmann R.A. In: Trost B.M., Fleming I., and Heathcock C.H. (Eds). Comprehensive Organic Synthesis Vol. 2 (1991), Pergamon Press, Oxford Chapter 4.3
6. Bloch R. Chem. Rev. 98 (1998) 1407-1438
7. For reviews on the asymmetric nucleophilic addition to imines, see:. Enders D., and Reinhold U. Tetrahedron: Asymmetry 8 (1997) 1895-1946
8. Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069-1094
9. Charette A.B., Boezio A.A., Côté A., Moreau E., Pytkowicz J., Desrosiers J.-N., and Legault C. Pure Appl. Chem. 77 (2005) 1259-1267
10. Vilaivan T., Bhanthumnavin W., and Sritana-Anant Y. Curr. Org. Chem. 9 (2005) 1315-1392
11. For a review on the use of N-phosphinoylimines in stereoselective synthesis, see:. Weinreb S.M., and Orr R.K. Synthesis (2005) 1205-1227
12. See, for instance:. Andersson P.G., Guijarro D., and Tanner D. J. Org. Chem. 62 (1997) 7364-7375
13. Knochel P. In: Trost B.M., Fleming I., and Shreiber S.L. (Eds). Comprehensive Organic Synthesis Vol. 1 (1991), Pergamon Press, Oxford Chapter 1.7
14. Erdik E. Organozinc Reagents in Organic Synthesis (1996), CRC Press, Boca Raton
15. Rozema M.J., Sidduri A., and Knochel P. J. Org. Chem. 57 (1992) 1956-1958
16. For a review, see:. Knochel P., and Singer R.D. Chem. Rev. 93 (1993) 2117-2188
17. Vettel S., Vaupel A., and Knochel P. Tetrahedron Lett. 36 (1995) 1023-1026
18. Vettel S., Vaupel A., and Knochel P. J. Org. Chem. 61 (1996) 7473-7481
19. Langer F., Schwink L., Devasagayaraj A., Chavant P.-Y., and Knochel P. J. Org. Chem. 61 (1996) 8229-8243
20. Micouin L., and Knochel P. Synlett (1997) 327-328
21. See, for instance:. Soai K., Hatanaka T., and Miyazawa T. J. Chem. Soc., Chem. Commun. (1992) 1097-1098
22. Suzuki T., Narisada N., Shibata T., and Soai K. Tetrahedron: Asymmetry 7 (1996) 2519-2522
23. Guijarro D., Pinho P., and Andersson P.G. J. Org. Chem. 63 (1998) 2530-2535
24. Jimeno C., Vidal-Ferran A., Moyano A., Pericàs M.A., and Riera A. Tetrahedron Lett. 40 (1999) 777-780
25. Brandt P., Hedberg C., Lawonn K., Pinho P., and Andersson P.G. Chem. Eur. J. 5 (1999) 1692-1699
26. Jimeno C., Reddy K.S., Solà L., Moyano A., Pericàs M.A., and Riera A. Org. Lett. 2 (2000) 3157-3159
27. Pinho P., and Andersson P.G. Tetrahedron 57 (2001) 1615-1618
28. Zhang H.-L., Zhang X.-M., Gong L.-Z., Mi A.-Q., Cui X., Jiang Y.-Z., Choi M.C.K., and Chan A.S.C. Org. Lett. 4 (2002) 1399-1402
29. Beresford K.J.M. Tetrahedron Lett. 43 (2002) 7175-7177
30. Zhang H.-L., Jiang F., Zhang X.-M., Cui X., Gong L.-Z., Mi A.-Q., Jiang Y.-Z., and Wu Y.-D. Chem. Eur. J. 10 (2004) 1481-1492
31. Beresford K.J.M. Tetrahedron Lett. 45 (2004) 6041-6044
32. Zhang X., Lin W., Gong L., Mi A., Cui X., Jiang Y., Choi M.C.K., and Chan A.S.C. Tetrahedron Lett. 43 (2002) 1535-1537
33. Zhang X.-M., Zhang H.-L., Lin W.-Q., Gong L.-Z., Mi A.-Q., Cui X., Jiang Y.-Z., and Yu K.-B. J. Org. Chem. 68 (2003) 4322-4329
34. Shi M., and Wang C.-J. Adv. Synth. Catal. 345 (2003) 971-973
35. Boezio A.A., and Charette A.B. J. Am. Chem. Soc. 125 (2003) 1692-1693
36. Boezio A.A., Pytkowicz J., Côté A., and Charette A.B. J. Am. Chem. Soc. 125 (2003) 14260-14261
37. Côté A., Boezio A.A., and Charette A.B. Angew. Chem., Int. Ed. 43 (2004) 6525-6528
38. Wang M.-C., Liu L.-T., Hua Y.-Z., Zhang J.-S., Shi Y.-Y., and Wang D.-K. Tetrahedron: Asymmetry 16 (2005) 2531-2534
39. Kim B.-S., Kang S.-W., Kim K.H., Ko D.-H., Chung Y., and Ha D.-C. Bull. Korean Chem. Soc. 26 (2005) 1501-1502
40. Porter J.R., Traverse J.F., Hoveyda A.H., and Snapper M.L. J. Am. Chem. Soc. 123 (2001) 984-985
41. Porter J.R., Traverse J.F., Hoveyda A.H., and Snapper M.L. J. Am. Chem. Soc. 123 (2001) 10409-10410
42. Burguete M.I., Collado M., Escorihuela J., Galindo F., Garcia-Verdugo E., Luis S.V., and Vicent M.J. Tetrahedron Lett. 44 (2003) 6891-6894
43. Almansa R., Guijarro D., and Yus M. Tetrahedron 63 (2007) 1167-1174
44. For some recent examples, see:. Xu Q., Wang H., Pan X., Chan A.S.C., and Yang T.-k. Tetrahedron Lett. 42 (2001) 6171-6173
45. Zhong G., Fan J., and Barbas C.F. Tetrahedron Lett. 45 (2004) 5681-5684
46. Liu X., and Fox J.M. J. Am. Chem. Soc. 128 (2006) 5600-5601
47. Wang G.-y., Liu X.-y., and Zhao G. Synlett (2006) 1150-1154
48. Li Y., Liu X., Yang Y., and Zhao G. J. Org. Chem. 72 (2007) 288-291
49. 2 = H) is enantiomeric with respect to our ligand 1.