Studies on diastereoselective reduction of cyclic β-ketoesters with boron hydrides. Part 4: The reductive profile of functionalized cyclohexanone derivatives

Tetrahedron

Volumn 60, Issue 12, 2004, Pages 2745-2755

  Fraga, Carlos A M ^a   Teixeira, Lis Helena P ^a   Menezes, Carla Maria De S ^a   Sant'Anna, Carlos Mauricio R ^a,b   Ramos, Maria Da Conceição K V ^a   De Aquino Neto, Francisco R ^a   Barreiro, Eliezer J ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b FEDERAL RURAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Boron hydrides; Diastereoselective reduction; Ketoesters

Indexed keywords

BORON; CARBONYL DERIVATIVE; CHELATING AGENT; CYCLOHEXANONE; ESTER; SODIUM BOROHYDRIDE;

ARTICLE; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 1542375287     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.079     Document Type: Article

References (48)

1. Benetti S., Romagnoli R., De Risi C., Spalluto G., Zanirato V. Chem Rev. 95:1995;1065-1114.
2. Ghosh A.K., Thompson W.J., Munson P.M., Liu W., Huff J. Bioorg. Med. Chem. Lett. 5:1995;83-88.
3. Cossy J., Ibhi S., Kahn P., Tacchini L. Tetrahedron Lett. 36:1995;7877-7880.
4. Keppens M., De Kimpe M. J. Org. Chem. 60:1995;3916-3918.
5. Fraga C.A.M., Barreiro E.J. Chirality. 8:1996;305-310.
6. Fraga C.A.M., Barreiro E.J., da Silva E.F., dos Santos A.R., Ramos M.C.K.V., de Aquino Neto F.R. Chirality. 9:1997;321-324.
7. Fraga C.A.M., Barreiro E.J. Synth. Commun. 25:1995;1133-1144.
8. Sant'Anna C.M.R., Alencastro R.B., Barreiro E.J., Fraga C.A. J. Mol. Struct. (Theochem). 340:1995;193-199.
9. Teixeira L.H.P., Barreiro E.J., Fraga C.A.M. Synth. Commun. 27:1997;3241-3257.
10. Teixeira L.H.P., de Souza M.C.B.V., Ramos M.C.K.V., de Aquino Neto F.R., Barreiro E.J., Fraga C.A.M. Synth. Commun. 32:2002;505-526.
11. Peçanha E.P., Fraga C.A.M., Barreiro E.J. Heterocycles. 48:1998;2621-2630.
12. Barreiro E.J., Fraga C.A.M., Peçanha E.P. Trends Heterocycl. Chem. 6:1999;37-48.
13. Santos M.R.L., Barreiro E.J., Braz-Filho R., Fraga C.A.M. Tetrahedron. 56:2000;5289-5295.
14. Peçanha E.P., Verli H., Rodrigues C.R., Barreiro E.J., Fraga C.A.M. Tetrahderon Lett. 43:2002;1607-1611.
15. Fraga C.A.M., Miranda A.L.P., Barreiro E.J. Chem. Pharm. Bull. 44:1996;2157-2161.
16. Peçanha E.P., Fraga C.A.M., de Sant'anna C.M.R., Miranda A.L.P., Barreiro E.J. Il Farmaco. 53:1998;327-336.
17. Peçanha E.P., Fraga C.A.M., Barreiro E.J. Quím. Nova. 20:1997;435-437.
18. Purchased from Aldrich Co, Milwaukee, USA.
19. Micovic V.M. Organic synthesis. Collect. Vol. 2:1943;. pp 264-265.
20. Araújo A.C.V., Almeida F.V., Bieber L.W. Quím. Nova. 19:1996;79-81.
21. Barco A., Benetti S., Pollini G.P. Synthesis. 1973;316.
22. Ramos M.C.K.V., Silva E.F., Aquino Neto F.R., Peçanha E.P., Rodrigues C.R., Barreiro E.J., Fraga C.A.M. Anal. Chem. 72:2000;3056-3062.
23. Ramos M.C.K.V., Teixeira L.H.P., Aquino Neto F.R., Barreiro E.J., Rodrigues C.R., Fraga C.A.M. J. Chromatogr. A. 985:2003;321-331.
24. Frater G. Helv. Chim. Acta. 63:1980;1383.
25. Stewart J.J.P. J. Comput. Chem. 10:1989;209-220.
26. Stewart J.J.P. J. Comput. Chem. 10:1989;221-264.
27. Stewart J.J.P. J. Comput. Chem. 12:1991;320-341.
28. Hehre W.J., Shusterman A.J., Nelson J.E. The molecular modeling workbook for organic chemistry. 1998;Wavefunction, Irvine. p 307.
29. Höltje H.-D., Folkers G. Manhold R., Kubinyi H., Timmerman H. Molecular modeling. Basic principles and applications. Vol. 5:1997;194 VCH, Weinheim.
30. Wigfield D.C. Tetrahedron. 35:1979;449-462.
31. Dalla V., Fonken G.J., Noyce D.S. Tetrahedron Lett. 40:1999;5193-5196.
32. Koskinen A.M.P., Koskinen T.M. Tetrahedron Lett. 34:1993;6765-6768.
33. Taniguchi M., Fujii H., Oshima K., Utimoto K. Tetrahedron. 49:1993;11169-11182.
34. Taniguchi M., Fujii H., Oshima K., Utimoto K. Tetrahedron. 51:1995;679-686.
35. Nakata T., Oishi T. Tetrahedron Lett. 21:1980;1641-1644.
36. Nakata T., Tanaka T., Oishi T. Tetrahedron Lett. 22:1980;4723-4726.
37. Brown, H. C.; Krishanamurthy, S. J. Am. Chem. Soc. 1972, 94, 7159-7161.
38. Raber D., Guida W.C. J. Org. Chem. 41:1976;690-696.
39. Akita H., Chen C.Y., Uchida K. Tetrahedron: Asymmetry. 1995;2131-2134.
40. Gung B.W. Chem. Rev. 99:1999;1377-1386.
41. Cimarelli C., Palmieri G. Tetrahedron: Asymmetry. 11:2000;2555-2563.
42. Hamed O., El-Qisairi A., Henry P.M. J. Org. Chem. 66:2001;180-185.
43. Tanabe Y. Bull. Chem. Soc. Jpn. 62:1989;1917-1924.
44. Pei T., Widenhoefer R.A. Chem. Commun. 2002;650-651. see supplementary data.
45. Padwa A., Kulkarni Y.S., Zhang Z. J. Org. Chem. 55:1990;4144-4153.
46. Ando K., Takemasa Y., Tomioka K., Koga K. Tetrahedron. 49:1993;1579-1588.
47. C-Alkylated derivative was obtained in the yields described here after its chromatographic separation from a mixture with the corresponding O-alkylated derivative (10%), by using a silica gel column and hexanes/AcOEt (from 99:1 to 95:5) as eluent.
48. Crabbé P., Garcia G.A., Ríus C. J. Chem. Soc., Perkin Trans. 1. 1973;810-816.