Synthesis of 2-amino-1,3-diols incorporating the cyclobutane ring

Tetrahedron

Volumn 64, Issue 38, 2008, Pages 9088-9092

  Pérez Fernández, Marta ^a   Avenoza, Alberto ^a   Busto, Jesús H ^a   Peregrina, Jesús M ^a   Rodríguez, Fernando ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1,3 DIOL DERIVATIVE; BROMINE DERIVATIVE; CYCLOBUTANE; CYCLOBUTANONE DERIVATIVE; METHYLMAGNESIUM BROMIDE; SOLVENT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SYNTHESIS;

EID: 48549094668     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.016     Document Type: Article

References (31)

1. Namyslo J.C., and Kaufmann D.E. Chem. Rev. 103 (2003) 1485-1537
2. Lee-Ruff E., and Mladenova G. Chem. Rev. 103 (2003) 1449-1483
3. Dembitsky V.M. J. Nat. Met. 62 (2008) 1-33
4. Hazelard D., Fadel A., and Girard C. Tetrahedron: Asymmetry 17 (2006) 1457-1464
5. Avenoza A., Busto J.H., Mata L., Peregrina J.M., and Pérez-Fernández M. Synthesis (2008) 743-746
6. Gauzy C., Saby B., Pereira E., Faure S., and Aitken D.J. Synlett (2006) 1394-1398
7. Basler B., Schuster O., and Bach T. J. Org. Chem. 70 (2005) 9798-9808
8. Marsac Y., Nourry A., Legoupy S., Pipelier M., Dubreuil D., Aubertin A.-M., Bourgougnon N., Benhida R., and Huet F. Tetrahedron 61 (2005) 7607-7612
9. Sharma A.K., Kumar P., and Gupta K.C. Helv. Chim. Acta 84 (2001) 3643-3649
10. Shi Y., Machida K., Kuzuya A., and Komiyama M. Bioconjugate Chem. 16 (2005) 306-311
11. Kashida H., Tanaka M., Baba S., Sakamoto T., Kawai G., Asanuma H., and Komiyama M. Chem.-Eur. J. 12 (2006) 777-784
12. Hsieh H.-P., Wu Y.-T., Chen S.-T., and Wang K.-T. Bioorg. Med. Chem. 7 (1999) 1797-1803
13. Avenoza A., Busto J.H., Canal N., and Peregrina J.M. Chem. Commun. (2003) 1376-1377
14. Avenoza A., Busto J.H., Canal N., and Peregrina J.M. J. Org. Chem. 70 (2005) 330-333
15. Jiménez-Osés G., Corzana F., Busto J.H., Pérez-Fernández M., Peregrina J.M., and Avenoza A. J. Org. Chem. 71 (2006) 1869-1878
16. Avenoza A., Busto J.H., Canal N., Peregrina J.M., and Pérez-Fernández M. Org. Lett. 7 (2005) 3597-3600
17. Avenoza A., Busto J.H., Canal N., García J.I., Jiménez-Osés G., Peregrina J.M., and Pérez-Fernández M. New J. Chem. 31 (2007) 224-229
18. Avenoza A., Busto J.H., Canal N., and Peregrina J.M. In: Iriepa I. (Ed). Structural Analysis of Cyclic Systems (2005), Research Signpost, Kerala 55-68
19. Avenoza A., Busto J.H., Peregrina J.M., and Pérez-Fernández M. Tetrahedron 61 (2005) 4165-4172
20. Carey A., and Sundberg R.J. Advanced Organic Chemistry. 4th ed. (2001), Kluwer Academic/Plenum, New York, NY
21. Hatano M., Matsumura T., and Ishihara K. Org. Lett. 7 (2005) 573-576
22. Knochel P., Dohle W., Gommermann N., Kneisel F.F., Kopp F., Korn T., Sapountzis I., and Anh Vu V. Angew. Chem., Int. Ed. 42 (2003) 4302-4320
23. Pérez-Ossorio R., Pérez-Rubalcaba A., Quiroga M.L., and Lasperas M. Tetrahedron Lett. 21 (1980) 1565-1566
24. Arjona O., Pérez-Ossorio R., Pérez-Rubalcaba A., and Quiroga M.L. J. Chem. Soc., Perkin Trans. 2 (1981) 597-603
25. Gurjar M.K., and Hotha S. Heterocycles 53 (2000) 1885-1889
26. ® column, Luna 5 μm C18(2) 100A, 250×4.6 mm. Injection volume=20 μL. Detector λ=254 nm. Retention times for cis-6 and trans-6 are 19.6 and 20.4 min, respectively.
27. Cherèst M., Felkin H., and Prudent N. Tetrahedron Lett. 18 (1968) 2199-2200
28. Anh N.T. Top. Curr. Chem. 88 (1980) 145-162
29. Avenoza A., Cativiela C., Corzana F., Peregrina J.M., and Zurbano M.M. Tetrahedron: Asymmetry 11 (2000) 2195-2204
30. Mengel A., and Reiser O. Chem. Rev. 99 (1999) 1191-1223
31. Wagner R., and Berger S. J. Magn. Reson., Ser. A 123 (1996) 119-121