Stereoselective synthesis of trans-4,5-disubstituted 1,3-imidazolidin-2-ones by reaction of an α-nitrogen carbanion with imines

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 428-429

  Kise, Naoki ^a,b   Kashiwagi, Kimiaki ^b   Watanabe, Mitsuru ^b   Yoshida, Jun Ichi ^b  

^a TOTTORI UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030029735     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951592k     Document Type: Article

References (36)

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7. The reaction of α-nitrogen carbanions formed from N-methyl-N-benzylphosphoramides with imines was previously reported. The results regarding diastereoselectivity, however, were not described: Savignac, P.; Leroux, Y.; Normant, H. Tetrahedron 1975, 31, 877.
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22. For recent reports, see: (a) Corey, E. J.; Jardine, P D.; Virgil, S.; Yuen, P. W.; Connell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (b) Dalko, P. I.; Langlois, Y. Tetrahedron Lett. 1992, 33, 5213. (c) Ahn, K. H.; Yoo, D. J.; Kim, J. S. Tetrahedron Lett. 1992, 33, 6661. (d) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (e) Nakajima, M.; Tomioka, K; Koga, K. Tetrahedron 1993, 49, 9735. (f) Mukaiyama, T.; Yamada, T.; Nagata, T.; Imagawa, K. Chem. Lett. 1993, 327. (g) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311 (h) Yoon, S. S.; Still, W. C. Tetrahedron Lett. 1994, 35, 2117.
23. For recent reports, see: (a) Corey, E. J.; Jardine, P D.; Virgil, S.; Yuen, P. W.; Connell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (b) Dalko, P. I.; Langlois, Y. Tetrahedron Lett. 1992, 33, 5213. (c) Ahn, K. H.; Yoo, D. J.; Kim, J. S. Tetrahedron Lett. 1992, 33, 6661. (d) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (e) Nakajima, M.; Tomioka, K; Koga, K. Tetrahedron 1993, 49, 9735. (f) Mukaiyama, T.; Yamada, T.; Nagata, T.; Imagawa, K. Chem. Lett. 1993, 327. (g) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311 (h) Yoon, S. S.; Still, W. C. Tetrahedron Lett. 1994, 35, 2117.
24. For recent reports, see: (a) Corey, E. J.; Jardine, P D.; Virgil, S.; Yuen, P. W.; Connell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (b) Dalko, P. I.; Langlois, Y. Tetrahedron Lett. 1992, 33, 5213. (c) Ahn, K. H.; Yoo, D. J.; Kim, J. S. Tetrahedron Lett. 1992, 33, 6661. (d) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (e) Nakajima, M.; Tomioka, K; Koga, K. Tetrahedron 1993, 49, 9735. (f) Mukaiyama, T.; Yamada, T.; Nagata, T.; Imagawa, K. Chem. Lett. 1993, 327. (g) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311 (h) Yoon, S. S.; Still, W. C. Tetrahedron Lett. 1994, 35, 2117.
25. For recent reports, see: (a) Corey, E. J.; Jardine, P D.; Virgil, S.; Yuen, P. W.; Connell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (b) Dalko, P. I.; Langlois, Y. Tetrahedron Lett. 1992, 33, 5213. (c) Ahn, K. H.; Yoo, D. J.; Kim, J. S. Tetrahedron Lett. 1992, 33, 6661. (d) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (e) Nakajima, M.; Tomioka, K; Koga, K. Tetrahedron 1993, 49, 9735. (f) Mukaiyama, T.; Yamada, T.; Nagata, T.; Imagawa, K. Chem. Lett. 1993, 327. (g) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311 (h) Yoon, S. S.; Still, W. C. Tetrahedron Lett. 1994, 35, 2117.
26. For recent reports, see: (a) Corey, E. J.; Jardine, P D.; Virgil, S.; Yuen, P. W.; Connell, R. D. J. Am. Chem. Soc. 1989, 111, 9243. (b) Dalko, P. I.; Langlois, Y. Tetrahedron Lett. 1992, 33, 5213. (c) Ahn, K. H.; Yoo, D. J.; Kim, J. S. Tetrahedron Lett. 1992, 33, 6661. (d) Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. (e) Nakajima, M.; Tomioka, K; Koga, K. Tetrahedron 1993, 49, 9735. (f) Mukaiyama, T.; Yamada, T.; Nagata, T.; Imagawa, K. Chem. Lett. 1993, 327. (g) Hosoya, N.; Hatayama, A.; Irie, R.; Sasaki, H.; Katsuki, T. Tetrahedron 1994, 50, 4311 (h) Yoon, S. S.; Still, W. C. Tetrahedron Lett. 1994, 35, 2117.
27. For recent reports, (a) Kawashita, M.; Hirata, R. Bull. Chem. Soc. Jpn. 1993, 66, 2002. (b) Brunner, H.; Schiessling, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 125.
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29. The stereoselective synthesis of optically active unsymmetrical 1,2-diamines from α-amino acids has been reported: Reetz, M. T.; Jaeger, R.; Drewlies, R.; Hubel, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 103.
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31. Sankhavasi, W.; Yamamoto, M.; Kohmoto, S.; Yamada, K. Bull. Chem. Soc. Jpn. 1991, 64, 1425.
32. It has been reported that the reactions of α-lithiated tetrahydroisoquinoline and piperidine derivatives with aromatic aldehydes showed low diastereoselectivities; (a) Seebach, D.; Syfrig, M. A. Angew. Chem., Int. Ed. Engl. 1984, 23, 248. (b) Rein, K. S.; Gawley, R. E. J. Org. Chem. 1991, 56, 1564. (c) Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109.
33. It has been reported that the reactions of α-lithiated tetrahydroisoquinoline and piperidine derivatives with aromatic aldehydes showed low diastereoselectivities; (a) Seebach, D.; Syfrig, M. A. Angew. Chem., Int. Ed. Engl. 1984, 23, 248. (b) Rein, K. S.; Gawley, R. E. J. Org. Chem. 1991, 56, 1564. (c) Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109.
34. It has been reported that the reactions of α-lithiated tetrahydroisoquinoline and piperidine derivatives with aromatic aldehydes showed low diastereoselectivities; (a) Seebach, D.; Syfrig, M. A. Angew. Chem., Int. Ed. Engl. 1984, 23, 248. (b) Rein, K. S.; Gawley, R. E. J. Org. Chem. 1991, 56, 1564. (c) Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109.
35. High threo selectivities have been reported in the reactions of α-lithiated dihydroindole and pyrrolidine amidines with aromatic aldehydes: (a) Meyers, A. I.; Hellring, S. Tetrahedron Lett. 1981, 22, 5119. (b) Sanner, M. A. Tetrahedron Lett. 1989, 30, 1909.
36. High threo selectivities have been reported in the reactions of α-lithiated dihydroindole and pyrrolidine amidines with aromatic aldehydes: (a) Meyers, A. I.; Hellring, S. Tetrahedron Lett. 1981, 22, 5119. (b) Sanner, M. A. Tetrahedron Lett. 1989, 30, 1909.