Anchimeric assistance in the case of vicinal dimesylate: Formation of enantiomeric or meso-bimorpholine

Synthesis

Volumn , Issue 11, 2006, Pages 1853-1857

  Kanger, Tõnis ^a   Laars, Marju ^a   Kriis, Kadri ^a   Kailas, Tiiu ^a   Müürisepp, Aleksander Mati ^a   Pehk, Tõnis ^b   Lopp, Margus ^a  

^a TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^b NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

Author keywords

Amines; Asymmetric synthesis; Cyclizations; Neighboring group effects; Stereoselectivity

Indexed keywords

AMINES; MOLECULAR STRUCTURE; REACTION KINETICS; SUBSTITUTION REACTIONS; SULFONATION; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; CYCLIZATIONS; NEIGHBORING-GROUP EFFECTS; STEREOSELECTIVITY;

STEREOCHEMISTRY;

MESO BIMORPHOLINE; MESYLIC ACID; MORPHOLINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIMERA; CYCLIZATION; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE;

EID: 33745169362     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926469     Document Type: Article

References (29)

1. (a) Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev. 2000, 100, 2159.
2. (b) Ma, Y.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. Org. Lett. 2003, 5, 2103.
3. (c) Mealy, M. J.; Luderer, M. R.; Bailey, W. F.; Sommer, M. B. J. Org. Chem. 2004, 69, 6042.
4. (d) Bassindale, M. J.; Crawford, J. J.; Henderson, K. W.; Kerr, W. J. Tetrahedron Lett. 2004, 45, 4175.
5. (a) Notz, W.; Tanaka, F.; Barbas, C. F. III Acc. Chem. Res. 2004, 37, 580.
6. (b) Andrey, O.; Alexakis, A.; Bernardinelli, Org. Lett. 2003, 5, 2559.
7. (c) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611.
8. Kanger, T.; Ausmees, K.; Müürisepp, A.-M.; Pehk, T.; Lopp, M. Synlett 2003, 1055.
9. Kanger, T.; Kriis, K.; Pehk, T.; Müürisepp, A.-M.; Lopp, M. Tetrahedron: Asymmetry 2002, 13, 857.
10. (a) Kriis, K.; Kanger, T.; Müürisepp, A.-M.; Lopp, M. Tetrahedron: Asymmetry 2003, 14, 2271.
11. (b) Kriis, K.; Kanger, T.; Lopp, M. Tetrahedron: Asymmetry 2004, 15, 2687.
12. (a) Dave, R.; Sasaki, N. A. Org. Lett. 2004, 6, 15.
13. (b) Brenner, E.; Baldwin, R. M.; Tamagnan, G. Org. Lett. 2005, 7, 937.
14. (c) Lanman, B. A.; Myers, A. Org. Lett. 2004, 6, 1045.
15. (d) Dastlik, K. A.; Sundermeier, U.; Johns, D. M.; Chen, Y.; Williams, R. M. Synlett 2005, 693.
16. (a) Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927.
17. (b) Kotsuki, H.; Kuzume, H.; Gohda, T.; Fukuhara, M.; Ochi, M.; Oishi, T.; Hirama, M.; Shiro, M. Tetrahedron: Asymmetry 1995, 6, 2221.
18. (c) Alexakis, A.; Tomassini, A.; Chouillet, C.; Roland, S.; Mangeney, P.; Bernardinelli, G. Angew. Chem. Int. Ed. 2000, 39, 4093.
19. Schneider, H. J.; Hoppen, V. J. Org. Chem. 1978, 43, 3866.
20. (a) Bentley, T. W.; Norman, S. J.; Gerstner, E.; Kemmer, R.; Christl, M. Chem. Ber. 1993, 126, 1749.
21. (b) Borodkin, G. I.; Pushkareva, O. A.; Gatilov, Y. V.; Shubin, V. G. Zh. Org. Khim. 1988, 24, 2505;
22. Chem. Abstr. 1989, 111, 77248.
23. (c) Borodkin, G. I.; Konradi, N. R.; Shubin, V. G. Zh. Org. Khim. 1987, 23, 1599;
24. Chem. Abstr. 1988, 108, 111510.
25. Raghavan, S.; Tony, K. A. J. Org. Chem. 2003, 68, 5002.
26. Knapp, S.; Kirk, B. A. Tetrahedron Lett. 2003, 44, 7601.
27. de Sousa, S. E.; O'Brien, P.; Steffens, H. C. Tetrahedron Lett. 1999, 40, 8423.
28. Dieter, R. K.; Deo, N.; Lagu, B.; Dieter, J. W. J. Org. Chem. 1992, 57, 1663.
29. Rosen, T.; Fesik, S. W.; Chu, D. T.; Pernet, A. G. Synthesis 1988, 40.