Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde

Tetrahedron Asymmetry

Volumn 18, Issue 19, 2007, Pages 2349-2357

  Tanyeli, Cihangir ^a   Odabaş, Serhat ^a   Erdem, Mine ^a   Çakir, Esen ^a   Keskin, Eda ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

1 [3 [(DIMETHYLAMINO)METHYL]BICYCLO[2.2.1]HEPT 5 EN 2 YL]CYCLOHEXANOL; 1 [3 [(DIMETHYLAMINO)METHYL]BICYCLO[2.2.1]HEPT 5 EN 2 YL]CYCLOPENTANOL; 1,4 AMINOALCOHOL; 2 [3 [(DIMETHYLAMINO)METHYL]BICYCLO[2.2.1]HEPT 5 EN 2 YL]PROPAN 2 OL; 3 [3 [(DIMETHYLAMINO)METHYL]BICYCLO[2.2.1]HEPT 5 EN 2 YL]PENTAN 3 OL; [3 (MORPHOLINOMETHYL)BICYCLO[2.2.1]HEPT 5 EN 2 YL]METHANOL; [3 (PIPERIDIN 1 YLMETHYL)BICYCLO[2.2.1]HEPT 5 EN 2 YL]METHANOL; [3 (PYRROLIDIN 1 YLMETHYL)BICYCLO[2.2.1]HEPT 5 EN 2 YL]METHANOL; [3 [(2 AMINOPHENYLAMINO)METHYL]BICYCLO[2.2.1]HEPTAN 2 YL]METHANOL; [3 [(2 CHLOROPHENYLAMINO)METHYL]BICYCLO[2.2.1]HEPTAN 2 YL]METHANOL; [3 [(DIALLYLAMINO)METHYL]BICYCLO[2.2.1]HEPT 5 EN 2 YL]METHANOL; [3 [(DIBENZYLAMINO)METHYL]BICYCLO[2.2.1]HEPT 5 EN 2 YL]METHANOL; [3 [(DIMETHYLAMINO)METHYL]BICYCLO[2.2.1]HEPT 5 EN 2 YL]METHANOL; [3 [(PHENYLAMINO)METHYL]BICYCLO[2.2.1]HEPTAN 2 YL]METHANOL; AMINE; AMINOALCOHOL; ANILINE; ANILINE DERIVATIVE; AROMATIC AMINE; BENZALDEHYDE; DIETHYLZINC; LIGAND; N [[3 (HYDROXYMETHYL)BICYCLO[2.2.1]HEPTAN 2 YL]METHYL] 4 METHYLBENZENESULFONAMIDE; NORBORNANE DERIVATIVE; NORBORNENE DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CIS ISOMER; GRIGNARD REACTION; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 35348826787     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.09.019     Document Type: Article

References (44)

1. Corey E.J., and Hannon F.J. Tetrahedron Lett. 28 (1987) 5237-5240
2. Zhang H., Xue F., Mak T.C.W., and Chan K.S. J. Org. Chem. 61 (1996) 8002-8003
3. Zhang H., and Chan K.S. J. Chem. Soc., Perkin Trans. 1 (1999) 381-382
4. Kang S.-W., Ko D.-H., Kim K.H., and Ha D.-C. Org. Lett. 5 (2003) 4517-4519
5. For reviews of 1,2-aminoalcohols as chiral auxiliaries, see:. Ager D.J., Prakash I., and Schaad D.R. Chem. Rev. 96 (1996) 835-875
6. Senanayake C.H. Aldrichim. Acta 31 (1998) 3-15
7. Fache F., Schulz E., Tommasino M.L., and Lemaire M. Chem. Rev. 100 (2000) 2159-2231
8. For reviews of 1,3-aminoalcohols, see:. Lait S.M., Rankic D.A., and Keay B.A. Chem. Rev. 107 (2007) 767-796
9. Oguni N., and Omi T. Tetrahedron Lett. 25 (1984) 2823-2824
10. Kitamura M., Suga S., Kawai K., and Noyori R. J. Am. Chem. Soc. 108 (1986) 6071-6072
11. Kitamura M., Okada S., Suga S., and Noyori R. J. Am. Chem. Soc. 111 (1989) 4028-4036
12. Noyori R., Suga S., Kaway K., Okada S., Kitamura M., Oguni N., Hayashi N., Kaneko T., and Matsuda Y. J. Organomet. Chem. 382 (1990) 19-37
13. Noyori R., and Kitamura M. Angew. Chem., Int. Ed. Engl. 30 (1991) 49-69
14. Kitamura M., Suga S., Niwa M., and Noyori R. J. Am. Chem. Soc. 117 (1995) 4832-4842
15. Yamakawa M., and Noyori R. J. Am. Chem. Soc. 117 (1995) 6327-6335
16. Kitamura M., Suga S., Oka H., and Noyori R. J. Am. Chem. Soc. 120 (1998) 9800-9809
17. Yamakawa M., and Noyori R. Organometallics 18 (1999) 128-133
18. Noyori R. Angew. Chem., Int. Ed. 41 (2002) 2008-2022
19. Beliczey J., Giffels G., Kragl U., and Wandrey C. Tetrahedron: Asymmetry 8 (1997) 1529-1530
20. Sola L., Vidal-Ferran A., Moyano A., Perkas M.A., and Riera A. Tetrahedron: Asymmetry 8 (1997) 1559-1568
21. Cho B.T., and Chun Y.S. Tetrahedron: Asymmetry 9 (1998) 1489-1492
22. Nugent A.W. J. Chem. Soc., Chem. Commun. (1999) 1369-1370
23. Genov M., Kostova K., and Dimitrov V. Tetrahedron: Asymmetry 8 (1997) 1869-1876
24. Genov M., Dimitrov V., and Ivanova V. Tetrahedron: Asymmetry 8 (1997) 3703-3706
25. Knollmüller M., Ferencic M., and Gärtner P. Tetrahedron: Asymmetry 10 (1999) 3969-3975
26. Hanyu N., Aoki T., Mino T., Sakamoto M., and Fujita T. Tetrahedron: Asymmetry 11 (2000) 2971-2979
27. Scarpi D., Galbo F.L., Occhiato E.G., and Guarna A. Tetrahedron: Asymmetry 15 (2004) 1319-1324
28. Faux N., Razafimahefa D., Picart-Goetgheluck S., and Brocard J. Tetrahedron: Asymmetry 16 (2005) 1189-1197
29. Kasashima Y., Hanyu N., Aoki T., Mino T., Sakamoto M., and Fujita T. J. Oleo Sci. 54 (2005) 495-504
30. Zhong J., Wang M., Guo H., Yin M., Bian Q., and Wang M. Synlett (2006) 1667-1670
31. Martinez A.G., Vilar E.T., Fraile A.G., Cerero S.M., Ruiz P.M., and Morillo C.D. Tetrahedron: Asymmetry 18 (2007) 742-749
32. He X.C., and Eliel E.L. Tetrahedron 43 (1987) 4979-4987
33. Goldfuss B., Steigelman M., Khan S.I., and Houk K.N. J. Org. Chem. 65 (2000) 77-82
34. Hanyu N., Aoki T., Mino T., Sakamoto M., and Fujita T. Tetrahedron: Asymmetry 11 (2000) 4127-4136
35. Steiner D., Sethofer S.D., Goralski C.T., and Singaram B. Tetrahedron: Asymmetry 13 (2002) 1477-1483
36. Tanyeli C., and Sünbül M. Tetrahedron: Asymmetry 16 (2005) 2039-2043
37. Bolm C., Gerlach A., and Dinter C.L. Synlett (1999) 195-196
38. Bolm C., Schiffers I., Dinter C.L., and Gerlach A. J. Org. Chem. 65 (2000) 6984-6991
39. Bolm C., Schiffers I., Dinter C.L., Defrere L., Gerlach A., and Raabe G. Synthesis (2001) 1719-1730
40. Bolm C., Dinter C.L., Schiffers I., and Defrere L. Synlett (2001) 1875-1877
41. Bolm C., Schiffers I., Atodiresei I., Özçubukçu S., and Raabe G. New J. Chem. 27 (2003) 14-17
42. Bolm C., Schiffers I., Atodiresei I., and Hackenberger C.P.R. Tetrahedron: Asymmetry 14 (2003) 3455-3467
43. Middlemas E.D., and Quin L.D. J. Org. Chem. 44 (1979) 2587-2589
44. Tanyeli C., and Özçubukçu S. Tetrahedron: Asymmetry 14 (2003) 1167-1170