Diastereoselective 1,3-dipolar cycloadditions with enantiopure azomethine ylids

Tetrahedron

Volumn 54, Issue 36, 1998, Pages 10733-10752

  Enders, Dieter ^a   Meyer, Ilka ^a   Runsink, Jan ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2,2 DIMETHYL 4 PHENYL 1,3 DIOXAN 5 YLAMINE; ALDEHYDE; AMINE; AZOMETHINE YLID; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032480391     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00638-3     Document Type: Article

References (27)

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3. [2] Figadère, B.; Pichon, M. Tetrahedron: Asymmetry 1996, 7, 927-964. For a general review concerning 1,3-dipolar cycloadditions see: Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863-909.
4. [3] Wittland, D.; Flörke, U.; Risch, N. Synthesis 1997, 1291-1295.
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6. b) Anslow, A. S.; Harwood, L. M.; Phillips, H.; Watkin, D.; Wong, L.F. Tetrahedron: Asymmetry 1991, 2, 1343-1358. -
7. c) Harwood, L. M.; Marco, J.; Watkin, D.; Williams, E.; Wong, L. F. Tetrahedron: Asymmetry 1992, 3, 1127-1130. -
8. d) Williams, R. M.; Zhai, W.; Aldous, D. J. J. Org. Chem. 1992, 57, 6527-6532. -
9. e) Harwood, L. M.; Manage, A. C.; Robin, S.; Hopes, S. F. G.; Watkin, D. J.; Williams, C. E. Synlett 1993, 777-780. -
10. f) Harwood, L. M.; Lilley, I. A. Tetrahedron Lett. 1993, 34, 537-540. -
11. g) Baldwin, J. E.; MacKenzie Turner, S. C.; Moloney, M. G. Synlett 1994, 925-928. -
12. h) Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 1557-1560. -
13. i) Anslow, A. S.; Harwood, L. M.; Lilley, I. A. Tetrahedron: Asymmetry 1995, 6, 2465-2468. -
14. j) Novello, F.; Prato, M.; Da Ros, T.; De Amici, M.; Bianco, A.; Toniolo, C.; Maggini, M. Chem. Commun. 1996, 903-904.
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17. [7] Refers to the exo isomer.
18. [8] Refers to the endo isomer.
19. 1H NMR spectroscopy.
20. [10] Complete separation of the exo/endo isomers by preparative HPLC.
21. [11] Separation of the exo/endo isomers by column chromatography.
22. [12] Determined by analytical HPLC.
23. [13] Separation of the exo/endo isomers by crystallization.
24. [14] Complete separation of the exo/endo isomers failed, 13% of the exo isomer were present.
25. [15] Complete separation of the exo/endo isomers failed, 18% of the exo isomer were present.
26. [16] (3S,4S,6S,6aR,9aS,9bS) refers to exo-6 and (3S,4S,6S,6aS,9aR,9bS) to endo-6.
27. [17] Hall, S. R.; Flack, H. D.; Stewart, J. M.; Eds. XTAL3.2 Reference Manual. Universities of Western Australia, Geneva and Maryland. Lamb: Perth 1992.