Stereoselective construction of the 1,1,1-trifluoroisopropyl moiety by asymmetric hydrogenation of 2-(trifluoromethyl)allylic alcohols and its application to the synthesis of a trifluoromethylated amino diol

Tetrahedron

Volumn 63, Issue 48, 2007, Pages 11965-11972

  Chen, Qi ^a   Qing, Feng Ling ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b DONGHUA UNIVERSITY   (China)

Author keywords

Amino diols; Asymmetric hydrogenation; Trifluoromethylated compounds

Indexed keywords

1,1,1 TRIFLUOROISOPROPYL; 2 (TRIFLUOROMETHYL)ALLYLIC ALCOHOL; 2,2 DIMETHYL 1,3 DIOXOLANE 4 CARBOXALDEHYDE; 3,3,3 TRIFLUOROISOPROPENYLLITHIUM; 4 TRIFLUOROMETHYL 1 AMINOPENTANE 2,3 DIOL; FLUORINATED QUASSINOID; ORGANOFLUORINE DERIVATIVE; TRIFLUOROLEUCINE; TRIFLUOROVALINE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; HYDROGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 35348834736     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.013     Document Type: Article

References (48)

1. Hunter L., O'Hagan D., and Slawin A.M.Z. J. Am. Chem. Soc. 128 (2006) 16422
2. Prakash G.K.S., and Beier P. Angew. Chem., Int. Ed. 45 (2006) 2172
3. Pihko P.M. Angew. Chem., Int. Ed. 45 (2006) 544
4. Billard T., and Langlois B.R. Eur. J. Org. Chem. (2007) 891
5. Mikami K., Itoh Y., and Yamanaka M. Chem. Rev. 104 (2004) 1
6. Ma J.A., and Cahard D. Chem. Rev. 104 (2004) 6119
7. Iseki K. Tetrahedron 54 (1998) 13887
8. For recent examples:
9. Hughes G., Devine P.N., Naber J.R., O'Shea P.D., Foster B.S., Mckay D.J., and Volante R.P. Angew. Chem., Int. Ed. 46 (2007) 1839
10. Massicot F., Monnier-Benoit M., Deka N., Plantier-Royon R., and Portella C. J. Org. Chem. 72 (2007) 1174
11. Song J.J., Tan Z., Xu J., Reeves J.T., Yee N.K., Ramdas R., Gallou F., Kuzmich K., DeLattre L., Lee H., Feng X., and Senanayake C.H. J. Org. Chem. 72 (2007) 292
12. Pedrosa R., Sayalero S., Vicente M., and Maestro A. J. Org. Chem. 71 (2006) 2177
13. Xing X., Fichera A., and Kumar K. J. Org. Chem. 67 (2002) 1722 and references therein
14. Ohno N., Fukamiya N., Okano M., Tagahara K., and Lee K.-H. Bioorg. Med. Chem. 5 (1997) 1489
15. Canney D.J., Lu H.-F., Mckeon A.C., Yoon K.-W., Xu K., Holland K.D., Rothman S.M., Ferrendelli J.A., and Covey D.F. Bioorg. Med. Chem. 6 (1998) 43
16. Jacobs R.T., Bernstein P.R., Cronk L.A., Vacek E.P., Newcomb L.F., Aharony D., Buckner C.K., and Kusner E.J. J. Med. Chem. 37 (1994) 1282
17. Hoffman W.F., Alberts A.W., Anderson P.S., Chen J.S., Smith R.L., and Willard A.K. J. Med. Chem. 29 (1986) 849
18. Tedesco R., Shaw A.N., Bambal R., Chai D., Concha N.O., Darcy M.G., Shanak D., Fitch D.M., Gates A., Gerhardt W.G., Halegoua D.L., Han C., Hofmann G.A., Wiggall K.J., Zimmerman M.N., and Duffy K.J. J. Med. Chem. 49 (2006) 971
19. Iseki K., Nagai T., and Kobayashi Y. Tetrahedron Lett. 34 (1993) 2169
20. Iseki K., Nagai T., and Kobayashi Y. Tetrahedron: Asymmetry 5 (1994) 961
21. Iseki K., Kuroki Y., Nagai T., and Kobayashi Y. Chem. Pharm. Bull. 44 (1996) 477
22. Iseki K., Kuroki Y., Nagai T., and Kobayashi Y. J. Fluorine Chem. 69 (1994) 5
23. Yamazaki T., Shinohara N., Kitazume T., and Sato S. J. Fluorine Chem. 97 (1999) 91
24. Koenig K.E., Bachman G.L., and Vineyard B.D. J. Org. Chem. 45 (1980) 2362
25. Burk M.J. J. Am. Chem. Soc. 113 (1991) 8518
26. Brown J.M. Angew. Chem., Int. Ed. Engl. 26 (1987) 190
27. Kitamura M., Kasahara I., Manabe K., Noyori R., and Takaya H. J. Org. Chem. 53 (1988) 708
28. Hong F., Tang X.Q., and Hu C.M. J. Chem. Soc., Chem. Commun. (1994) 631
29. Peng S., and Qing F.L. J. Chem. Soc., Perkin Trans. 1 (1999) 3345
30. Hanamoto T., and Fuchikami T. J. Org. Chem. 55 (1990) 4969
31. Optically active (R)-1a was obtained by chemical resolution of 1a: see Section 3.
32. Spero D.M., Kapadia S., and Farina V. Tetrahedron Lett. 36 (1995) 4543
33. Baker W.R., and Condon S.C. J. Org. Chem. 58 (1993) 3277
34. Kim S., Lee S., Lee T., Ko H., and Kim D. J. Org. Chem. 71 (2006) 8661
35. Liao J.Y., Tao J.H., Lin G.Q., and Liu D.G. Tetrahedron 61 (2005) 4715
36. Jaeger V., Huemmer W., Stahl U., and Gracza T. Synthesis (1991) 769
37. Fustero S., Jimenez D., Sanz-Cervera J.F., Sanchez-Rosello M., Esteban E., and Simon-Fuentes A. Org. Lett. 7 (2005) 3433
38. Prakash G.K.S., Mandal M., Schweizer S., Petasis N.A., and Olah G.A. J. Org. Chem. 67 (2002) 3718
39. Prakash G.K.S., Mandal M., Schweizer S., Petasis N.A., and Olah G.A. Org. Lett. 2 (2000) 3173
40. Peng S., and Qing F.L. J. Chem. Soc., Perkin Trans. 1 (1999) 3345
41. Jaeger V., Huemmer W., Stahl U., and Gracza T. Synthesis (1991) 771
42. Jaeger V., Schroeter D., and Koppenhoefer B. Tetrahedron 47 (1991) 2195
43. Badorrey R., Cativiela C., Diaz-de-Villegas M.D., and Galvez J.A. Synthesis (1997) 747
44. Drakesmith F.G., Stewart O.J., and Tarrant P. J. Org. Chem. 33 (1967) 280
45. For a review of chelation and non-chelation control in addition reactions of chiral α-alkoxy carbonyl compounds, see:. Reetz M.T. Angew. Chem., Int. Ed. Engl. 23 (1984) 556
46. Crystal data have been deposited at the Cambridge Crystallographic Data Center with reference number: CCDC 659319.
47. Coe J.W., and Roush W.R. J. Org. Chem. 54 (1980) 915
48. Miranda L.S.M., Meireles B.A., Costa J.S., Pereira V.L.P., and Vasconcellos M.L.A. Synlett (2005) 869