Asymmetric 1,3-dipolar cycloadditions of a chiral nonracemic glyoxylic azomethine imine

Tetrahedron Letters

Volumn 45, Issue 15, 2004, Pages 3127-3130

  Chung, Florence ^a   Chauveau, Ariane ^a   Seltki, Mohamed ^b   Bonin, Martine ^a   Micouin, Laurent ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

Author keywords

Asymmetric synthesis; Azomethine imine; Cycloadditions

Indexed keywords

ALIPHATIC COMPOUND; AROMATIC COMPOUND; IMINE; NONRACEMIC GLYOXYLIC AZOMETHINE IMINE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; COMPARATIVE STUDY; CYCLOADDITION; ELECTRON; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 1642345364     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.088     Document Type: Article

References (19)

1. Schreiber S.L. Science. 287:2000;1964-1969.
2. For a recent example of the use of 1,3-dipolar cycloadditions in diversity-oriented synthesis: Chen C., Li X., Schreiber S. J. Am. Chem. Soc. 125:2003;10174-10175.
3. For reviews on asymmetric 1,3-dipolar cycloadditions: Karlsson S., Hogberg H.E. Org. Prep. Proceed. Int. 33:2001;105-172.
4. Gothelf K.V., Jorgensen K.A. Chem. Rev. 98:1998;863-909.
5. Roussi F., Bonin M., Chiaroni A., Micouin L., Riche C., Husson H.-P. Tetrahedron Lett. 40:1999;3727-3730.
6. Roussi F., Chauveau A., Bonin M., Micouin L., Husson H.-P. Synthesis. 2000;1170-1179.
7. Chauveau A., Martens T., Bonin M., Micouin L., Husson H.-P. Synthesis. 2002;1885-1891.
8. Jacobi P.A., Martinelli M.J., Polanc S. J. Am. Chem. Soc. 106:1984;5594-5598.
9. Katayama H., Takatsu N., Kitano H., Shimaya Y. Chem. Pharm. Bull. 38:1990;1129-1135.
10. Grigg R., Rankovic Z., Thornton-Pett M., Somasunderam M. Tetrahedron. 49:1993;8679-8690.
11. Harwood L.M., Lilley I.A. Tetrahedron: Asymmetry. 6:1995;1557-1560.
12. Khau V.V., Martinelli M.J. Tetrahedron Lett. 37:1996;4323-4326.
13. Wittland C., Flörke U., Risch N. Synthesis. 1997;1291-1295.
14. 1H NMR of this solution (the high concentration of the reagent enables the direct NMR of the solution without the use of a deuterated solvent) shows that this aldehyde exists mainly as a trimeric form, and that the proportion of free aldehyde can be roughly estimated to 10%.
15. 2O in dipolar cycloadditions, see: Harwood L.M., Manage A.C., Robin S., Hopes S.F.G., Watkin D.J., Williams C.E. Synlett. 1997;777-780.
16. -3. Crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 225965 copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44 (0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ].
17. Houk K.N., Sims J., Duke R.E. Jr., Stozier R.W., Georges J.K. J. Am. Chem. Soc. 95:1973;7287-7301.
18. Houk K.N., Sims J., Watts C.R., Luskus L.J. J. Am. Chem. Soc. 95:1973;7301-7315.
19. -1): 1747, 1700. Elemental analysis. Calcd: C, 56.15; H, 5.46; N, 6.89. Found: C, 56.04; H, 5.49; N, 6.92.