Synthesis, reactivity and conformational stability of an l-phenylalanine derived oxadiazinanone

Tetrahedron Asymmetry

Volumn 17, Issue 16, 2006, Pages 2386-2392

  Dore, Delvis D ^a   Burgeson, James R ^a   Davis, Ryan A ^a   Hitchcock, Shawn R ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; ALDEHYDE; BENZENE DERIVATIVE; BENZYL DERIVATIVE; OXADIAZOLE DERIVATIVE; PHENYLALANINE; TITANIUM;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; PRIORITY JOURNAL; SYNTHESIS;

EID: 33749237479     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.09.002     Document Type: Article

References (21)

1. Hoover T.R., Groeper J.A., Parrott II R.W., Chandrashekar S.P., Finefield J.M., Dominguez A., and Hitchcock S.R. Tetrahedron: Asymmetry 17 (2006) 1831-1841
2. Hoover T.R., and Hitchcock S.R. Tetrahedron: Asymmetry 14 (2003) 3233-3241
3. Casper D.M., and Hitchcock S.R. Tetrahedron: Asymmetry 14 (2003) 517-521
4. Casper D.M., Burgeson J.R., Esken J.M., Ferrence G.M., and Hitchcock S.R. Org. Lett. 4 (2002) 3739-3742
5. Hitchcock S.R., Casper D.M., Vaughn J.F., Finefield J.M., Ferrence G.M., and Esken J.M. J. Org. Chem. 69 (2004) 714-718
6. Vaughn J.F., and Hitchcock S.R. Tetrahedron: Asymmetry 15 (2004) 3449-3455
7. Casper D.M., Blackburn J.R., Maroules C.D., Brady T., Esken J.M., Ferrence G.M., Standard J.M., and Hitchcock S.R. J. Org. Chem. 67 (2002) 8871-8876
8. Corminboeuf O., Quaranta L., Renaud P., Liu P., Jasperse C.P., and Sibi M.P. Chem.-Eur. J. 9 (2003) 28-35
9. Sibi M.P., Venkatraman L., Liu M., and Jasperse C.P. J. Am. Chem. Soc. 123 (2001) 8444-8445
10. Bull S.D., Davies S.G., Fox D.J., Garner A.C., and Sellers T.G.R. Pure Appl. Chem. 70 (1998) 1501-1506
11. Kanth J.V.B., and Periasamy M. J. Org. Chem. 56 (1991) 5964-5965
12. McKennon M.J., Meyers A.I., Drauz K., and Schwarm M. J. Org. Chem. 58 (1993) 3568-3571
13. In: Baxter E.W., Reitz A.B., and Overman L.E. (Eds). Org. React. 59 (2002) 3-714
14. Ghosh A.K., Hussain K.A., and Fidanze S. J. Org. Chem. 62 (1997) 6080-6082
15. It must be noted that this process was capricious and the generation of consistent yields was sometimes problematic.
16. Takacs J.M., Jaber M.R., and Vellekoop A.S. J. Org. Chem. 63 (1998) 2742-2748
17. Oppolzer W., Blagg J., Rodriguez I., and Walther E. J. Am. Chem. Soc. 112 (1990) 2767-2772
18. The (2R,3R)-enantiomer was derived from a previous oxadiazinanone study. Please see Ref. 4.
19. Zimmerman H.E., and Traxler M.D. J. Am. Chem. Soc. 79 (1957) 1920-1923
20. Rodrigues A., Olivato P.R., Zukerman-Schpector J., and Rittner R. Z. Kristallogr. 221 (2006) 226-230
21. Rodrigues A., Olivato P.R., and Rittner R. Synthesis (2005) 2578-2582