Highly Stereoselective Addition of Organomagnesium Reagents to Aziridinyl-2-carboxaldimine: Preparation of Enantiopure 2-Aminomethylaziridines and 4,5-Disubstituted Imidazolidin-2-ones

Synlett

Volumn , Issue 3, 2004, Pages 489-492

  Suh, Man Jin ^a   Kim, Sang Woo ^a,b   Beak, Seong In ^a   Ha, Hyun Joon ^a,b   Lee, Won Koo ^c  

^a Hankuk University of Foreign Studies   (South Korea)

^b Yonsei University   (South Korea)

^c Sogang University   (South Korea)

Author keywords

Addition reactions; Aziridines; Imines; Organometallic reagents; Stereoselectivity

Indexed keywords

ALCOHOL; AZIRIDINE; IMIDAZOLIDINE DERIVATIVE; IMINE; IONOTROPIC RECEPTOR; MAGNESIUM DERIVATIVE; REAGENT;

ADDITION REACTION; ARTICLE; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 1442311143     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815444     Document Type: Article

References (33)

1. For reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. (b) Zwanenburg, B.; ten Holte, P. In Stereoselective Heterocyclic Chemistry III; Metz, P., Ed.; Springer: Berlin, 2001, 93-124. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (d) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II, Vol. 1A; Padwa, A., Ed.; Pergamon Press: New York, 1996, 1. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
2. For reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. (b) Zwanenburg, B.; ten Holte, P. In Stereoselective Heterocyclic Chemistry III; Metz, P., Ed.; Springer: Berlin, 2001, 93-124. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (d) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II, Vol. 1A; Padwa, A., Ed.; Pergamon Press: New York, 1996, 1. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
3. For reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. (b) Zwanenburg, B.; ten Holte, P. In Stereoselective Heterocyclic Chemistry III; Metz, P., Ed.; Springer: Berlin, 2001, 93-124. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (d) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II, Vol. 1A; Padwa, A., Ed.; Pergamon Press: New York, 1996, 1. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
4. For reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. (b) Zwanenburg, B.; ten Holte, P. In Stereoselective Heterocyclic Chemistry III; Metz, P., Ed.; Springer: Berlin, 2001, 93-124. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (d) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II, Vol. 1A; Padwa, A., Ed.; Pergamon Press: New York, 1996, 1. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
5. For reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. (b) Zwanenburg, B.; ten Holte, P. In Stereoselective Heterocyclic Chemistry III; Metz, P., Ed.; Springer: Berlin, 2001, 93-124. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (d) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II, Vol. 1A; Padwa, A., Ed.; Pergamon Press: New York, 1996, 1. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
6. For reviews, see: (a) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. (b) Zwanenburg, B.; ten Holte, P. In Stereoselective Heterocyclic Chemistry III; Metz, P., Ed.; Springer: Berlin, 2001, 93-124. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347. (d) Osborn, H. M. I.; Sweeney, J. B. Tetrahedron: Asymmetry 1997, 8, 1693. (e) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II, Vol. 1A; Padwa, A., Ed.; Pergamon Press: New York, 1996, 1. (f) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
7. Lee, W.-K.; Ha, H.-J. Aldrichimica Acta 2003, 36, 57.
8. Hwang, G. I.; Chung, J.-H.; Lee, W. K. J. Org. Chem. 1996, 67, 6183.
9. Yun, J. M.; Sim, T. B.; Hahm, H. S.; Lee, W. K.; Ha, H.-J. J. Org. Chem. 2003, 68, 7675.
10. For reviews, see: (a) Alvoro, G.; Savoia, D. Synlett 2002, 651. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Ender, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) For recent examples, see: Saito, S.; Hatanaka, K.; Yamamoto, H. Synlett 2001, 1859. (e) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (f) Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
11. For reviews, see: (a) Alvoro, G.; Savoia, D. Synlett 2002, 651. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Ender, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) For recent examples, see: Saito, S.; Hatanaka, K.; Yamamoto, H. Synlett 2001, 1859. (e) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (f) Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
12. For reviews, see: (a) Alvoro, G.; Savoia, D. Synlett 2002, 651. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Ender, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) For recent examples, see: Saito, S.; Hatanaka, K.; Yamamoto, H. Synlett 2001, 1859. (e) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (f) Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
13. For reviews, see: (a) Alvoro, G.; Savoia, D. Synlett 2002, 651. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Ender, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) For recent examples, see: Saito, S.; Hatanaka, K.; Yamamoto, H. Synlett 2001, 1859. (e) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (f) Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
14. For reviews, see: (a) Alvoro, G.; Savoia, D. Synlett 2002, 651. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Ender, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) For recent examples, see: Saito, S.; Hatanaka, K.; Yamamoto, H. Synlett 2001, 1859. (e) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (f) Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
15. For reviews, see: (a) Alvoro, G.; Savoia, D. Synlett 2002, 651. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Ender, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) For recent examples, see: Saito, S.; Hatanaka, K.; Yamamoto, H. Synlett 2001, 1859. (e) Wang, D.-K.; Dai, L.-X.; Hou, X.-L.; Zhang, Y. Tetrahedron Lett. 1996, 37, 4187. (f) Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
16. Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem. Int. Ed. 1998, 37, 2580.
17. (a) Shimizu, M.; Suzuki, I.; Makino, H. Synlett 2003, 1635.
18. (b) Bhattarai, K.; Cainelli, G.; Panunzio, M. Synlett 1990, 229.
19. (c) Jacob, P.; Callery, P. S.; Shulgin, A. T.; Castagnoli, N. J. Org. Chem. 1976, 41, 3627.
20. (a) Alvaro, G.; Pacioni, P.; Savoia, D. Chem.-Eur. J. 1997, 3, 726.
21. (b) Wada, M.; Sakurai, Y.; Akiba, K.-y. Tetrahedron Lett. 1984, 25, 1079.
22. Park, C. S.; Kim, M. S.; Sim, T. B.; Pyun, D. K.; Lee, C. H.; Choi, D.; Lee, W. K.; Chang, J.-W.; Ha, H.-J. J. Org. Chem. 2003, 68, 43.
23. (a) Alexakis, A.; Lensen, N.; Mangeney, P. Tetrahedron Lett. 1991, 32, 1171.
24. (b) Alexakis, A.; Lensen, N.; Tranchier, J.-P.; Mangeney, P. J. Org. Chem. 1992, 57, 4563.
25. (c) Alexakis, A.; Lensen, N.; Tranchier, J.-P.; Pierre, M.; Mangeney, P. ; Feneau-Dupont, J.; Declercq, J. P. Synthesis 1995, 1038.
26. (d) Alexakis, A.; Tranchier, J.-P.; Lensen, N.; Mangeney, P. J. Am. Chem. Soc. 1995, 117, 10767.
27. Sapse, A. M.; Bunce, J. D.; Jain, D. C. J. Am. Chem. Soc. 1984, 106, 6579.
28. Dong, Y.; Yun, H.; Park, C. S.; Lee, W.-K.; Ha, H.-J. Acta Crystallogr., Sect. C 2003, 59, 659.
29. (a) Lim, Y.; Lee, W. K. Tetrahedron Lett. 1995, 36, 8431.
30. (b) Hayashi, K.; Nunami, K.-i.; Kato, J.; Yoneda, N.; Kubo, M.; Ochiai, T.; Ishida, R. J. Med. Chem. 1989, 32, 289.
31. (c) Shidari, M.; Pusino, A.; Gessa, C.; Cacco, G. J. Agric. Food Chem. 1998, 46, 2800.
32. (d) Robinson, R. P.; Laird, E. R.; Donahue, K. M.; Lopresti-Morrow, L. L.; Mitchell, P. G.; Reese, M. R.; Reeves, L. M.; Rouch, A. I.; Stam, E. J.; Yocum, S. A. Bioorg. Med. Chem. Lett. 2001, 11, 1211.
33. (e) Yasar, S.; Bergman, J.; Munzar, P.; Redhi, G.; Tober, C.; Knobel, N. ; Zschiesche, M.; Paronis, C. Eur. J. Pharm. 2003, 465, 257.