2-exo- versus 2-endo-Hydroxyl in δ-amino norbornan-2-ol-based catalysts: Investigating the role of the C(2) configuration in the asymmetric induction

Tetrahedron Asymmetry

Volumn 15, Issue 5, 2004, Pages 753-756

  García Martínez, Antonio ^a   Teso Vilar, Enrique ^b   García Fraile, Amelia ^b   De La Moya Cerero, Santiago ^a   Lora Maroto, Beatriz ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 (DIMETHYLAMINO)ETHYL] 2,3,3 TRIMETHYLBORNAN 2 OL; ALCOHOL DERIVATIVE; BENZALDEHYDE; DIETHYLZINC; HYDROXYL GROUP; KETONE DERIVATIVE; LIGAND; NORBORNANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; EPIMER; MOLECULAR MODEL; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 1442277241     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.12.014     Document Type: Article

References (29)

1. Some selected publications are: Kitamura M., Suga S., Kawai K., Noyori R. J. Am. Chem. Soc. 108:1986;6071.
2. Kitamura M., Okada S., Suga S., Noyori R. J. Am. Chem. Soc. 111:1989;4028.
3. Noyori R., Suga S., Kawai K., Okada S., Kitamura M., Oguni N., Hayashi M., Kaneko T., Matsuda Y. J. Organomet. Chem. 382:1990;19.
4. Noyori R., Kitamura M. Angew. Chem., Int. Ed. Engl. 30:1991;49.
5. Kitamura M., Suga S., Niwa M., Noyori R. J. Am. Chem. Soc. 117:1995;4832.
6. Yamakawa M., Noyori R. J. Am. Chem. Soc. 117:1995;6327.
7. Kitamura M., Suga S., Oka H., Noyori R. J. Am. Chem. Soc. 120:1998;9800.
8. Yamakawa M., Noyori R. Organometallics. 18:1999;128.
9. R Noyori Angew. Chem., Int. Ed. 41:2002;2008.
10. For example see: Guijarro D., Pinho P., Andersson P.G. J. Org. Chem. 63:1998;2530.
11. Chao B.T., Chun Y.S. Tetrahedron: Asymmetry. 9:1998;1489.
12. Nugent A.W. Chem. Commun. 1999;1369.
13. Kang J., Kim H.Y., Kim J.H. Tetrahedron: Asymmetry. 10:1999;2523.
14. Paleo R.M., Cabeza I., Sardina F.J. J. Org. Chem. 65:2000;2108.
15. Rasmusen T., Norrby P.-O. J. Am. Chem. Soc. 123:2001;2464.
16. García Martínez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., Martínez Ruiz P., Chicharro Villas P. Tetrahedron: Asymmetry. 13:2002;1.
17. García Martínez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., Martínez-Ruiz P. Tetrahedron: Asymmetry. 13:2002;1457.
18. Some recent examples are: Hanyu N., Aoki T., Mino T., Sakamoto M., Fujita T. Tetrahedron: Asymmetry. 11:2000;2971.
19. Hanyu N., Aoki T., Mino T., Sakamoto M., Fujita T. Tetrahedron: Asymmetry. 11:2000;4127.
20. Hanyu N., Mino T., Sakamoto M., Fujita T. Tetrahedron Lett. 41:2000;4587.
21. Panev S., Linden A., Dimitrov V. Tetrahedron: Asymmetry. 12:2001;1313.
22. Nevaleinen M., Nevaleinen V. Tetrahedron: Asymmetry. 12:2001;1772.
23. Panda M., Phuan P.-W., Kozlowski M.C. J. Org. Chem. 68:2003;564.
24. García Martínez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., Lora Maroto B. Tetrahedron: Asymmetry. 14:2003;1959.
25. García Martínez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., Lora Maroto B. Tetrahedron Lett. 43:2002;1183.
26. García Martínez A., Teso Vilar E., García Fraile A., de la Moya Cerero S., Lora Maroto B. Tetrahedron: Asymmetry. 13:2002;17. and references cited therein. Also see Ref. 5.
27. de la Moya Cerero S., García Martínez A., Teso Vilar E., García Fraile A., Lora Maroto B. J. Org. Chem. 68:2003;1451. and references cited therein.
28. +-43, 1). 140(2), 58 (100).
29. The enantiomer described by Fujita in Ref. [3b] is not (+)-epi- 8, but the (-) one. We have used the (+) one for making easier the comparison study with 8.