Convenient methods to access chiral camphanyl amine derivatives by sodium borohydride reduction of d -(-)-camphorquinone imines

Synthesis (Germany)

Volumn 44, Issue 20, 2012, Pages 3185-3190

  Periasamy, Mariappan ^a   Sanjeevakumar, Nalluri ^a   Reddy, Polimera Obula ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

chirality; diamines; diimines; reduction; sodium borohydride

Indexed keywords

AMINE DERIVATIVES; AMINO ALCOHOLS; CAMPHORQUINONE; DIAMINES; DIIMINES; ETHYLENE DIAMINE; SODIUM BOROHYDRIDES;

CHIRALITY; ETHANOL; ETHYLENE; METHANOL; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; PROPYLENE; REDUCTION;

SODIUM;

1,2 DIAMINOCYCLOHEXANE; 1,2 DIAMINOPROPANE; AMINE; AMINOALCOHOL; AMMONIA; CAMPHANYL AMINE DERIVATIVE; CAMPHORQUINONE IMINE DERIVATIVE; ETHANOL AMINE; ETHYLENEDIAMINE; EXO BORNYLAMINE; IMINE; METHANOL; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; PHYSICAL CHEMISTRY; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 84867334333     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1317012     Document Type: Article

References (38)

1. Kobayashi S., Ishitani H. Chem. Rev.: 1999; 99 1069
2. Kizirian J.-C. Chem. Rev.: 2008; 108 140
3. Luo Y., Zhang H., Wang Y., Xu P. Acc. Chem. Res.: 2010; 43 1317
4. Chelucci G. Chem. Soc. Rev.: 2006; 35 1230
5. García J. M., Maestro M. A., Oiarbide M., Odriozola J. M., Razkin J., Palomo C. Org. Lett.: 2009; 11 3826
6. Sugiura M., Mori C., Kobayashi S. J. Am. Chem. Soc.: 2006; 128 11038
7. Kloetzing R. J., Thaler T., Knochel P. Org. Lett.: 2006; 8 1125
8. Jeon S.-J, Chen Y. K., Walsh P. J. Org. Lett.: 2005; 7 1729
9. Busacca C. A., Grossbach D., Campbell S. C., Dong Y., Eriksson M. C., Harris R. E., Jones P. J., Kim J. Y., Lorenz J. C., McKellop K. B., OBrien E. M., Qiu F., Simpson R. D., Smith L., So R. C., Spinelli E. M., Vitous J., Zavattaro C. J. Org. Chem.: 2004; 69 5187
10. Blay G., Domingo L. R., Hernandez-Olmos V., Pedro J. R. Chem.-Eur. J.: 2008; 14 4725
11. Brues F., Kulhanek J., Ruzicka A. Tetrahedron Lett.: 2009; 50 3042
12. Xu Z., Wang R., Xu J., Da C., Yan W., Chen C. Org. Lett.: 2004; 6 1193
13. Li Y., Feng Z., You S.-L. Chem. Commun.: 2008; 2263
14. Li Y., Wang X.-Q, Feng Z., You S.-L. Chem. Commun.: 2008; 5823
15. Reddy P. V. G, Tabassum S., Blanrue A., Wilhelm R. Chem. Commun.: 2009; 5910
16. Lee S., Hartwig J. F. J. Org. Chem.: 2001; 66 3402
17. Sanjeevakumar N., Periasamy M. Tetrahedron: Asymmetry: 2009; 20 1842
18. Bonner M. P., Thornton E. R. J. Am. Chem. Soc.: 1991; 113 1299
19. Bosiak M. J., Krzeminski M. P., Jaisankar P., Zaidlewicz M. Tetrahedron: Asymmetry: 2008; 19 956
20. Periasamy M., Reddy M. N., Anwar S. Tetrahedron: Asymmetry: 2004; 15 1809
21. Periasamy M., Ramanathan C. R., Sampath Kumar N. Tetrahedron: Asymmetry: 1999; 10 2307
22. Rao Dharma V., Periasamy M. Tetrahedron: Asymmetry: 2000; 11 1151
23. Periasamy M., Devasagayaraj A., Satyanarayana N., Narayana C. Synth. Commun.: 1989; 19 565
24. Satishkumar S., Periasamy M. Tetrahedron: Asymmetry: 2006; 17 1116
25. Periasamy M., Bhaskar Kanth J. V., Bhanu Prasad A. S. Tetrahedron: 1994; 50 6411
26. Prasad A. B. S, Kanth J. V. B, Periassamy M. Tetrahedron: 1992; 48 4623
27. Kanth J. V. B, Periassamy M. J. Org. Chem.: 1991; 56 5964
28. Anwar S., Periasamy M. Tetrahedron: Asymmetry: 2006; 17 3244
29. Periasamy M., Muthukumaragopal G. P., Sanjeevakumar N. Tetrahedron Lett.: 2007; 48 6966
30. Periasamy M., Ramani G., Muthukumaragopal G. P. Synthesis: 2009; 1739
31. Vairaprakash P., Periasamy M. J. Org. Chem.: 2006; 71 3636
32. Vairaprakash P., Periasamy M. Tetrahedron Lett.: 2008; 49 1233
33. Periasamy M., Srinivas G., Suresh S. Tetrahedron Lett.: 2001; 42 7123
34. Giardina D., Gulini U., Massi M., Piloni M. G., Pompei P., Rafaiani G., Elchiorre C. J. Med. Chem.: 1993; 36 690
35. Hirokawa Y., Fujiwara I., Suzuki K., Harada H., Yoshikawa T., Yoshida N., Kato S. J. Med. Chem.: 2003; 46 702
36. Padmaja M., Periasamy M. Tetrahedron: Asymmetry: 2004; 15 2437
37. Dalai M., Periasamy M. Tetrahedron: Asymmetry: 2009; 20 1247
38. Alakonda L., Periasamy M. J. Organomet. Chem.: 2009; 694 3859