Nucleophilic substitution of (sulfonyloxymethyl)aziridines: an asymmetric synthesis of both isomers of mexiletine

Tetrahedron

Volumn 64, Issue 49, 2008, Pages 11110-11114

  Han, Sang Mi ^a   Ma, Sang ho ^a,b   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

(Sulfonyloxymethyl)aziridines; Chiral aziridine; Mexiletine; Nucleophilic substitution; Stereochemistry

Indexed keywords

[(2,6 DIMETHYLPHENOXY)METHYL] 1 [1 PHENYLETHYL]AZIRIDINE; AZIDOMETHYL 1 [1 PHENYLETHYL]AZIRIDINE; AZIRIDINE DERIVATIVE; BENZYL 1 [1 PHENYLETHYL]AZIRIDINE; METHOXYMETHYL 1 [1 PHENYLETHYL]AZIRIDINE; MEXILETINE; THIOCYANATOMETHYL 1 [1 PHENYLETHYL]AZIRIDINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY; SUBSTITUTION REACTION;

EID: 54549089734     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.068     Document Type: Article

References (27)

1. Tanner D. Angew. Chem., Int. Ed. Engl. 33 (1994) 599
2. Pearson W.H., Lian B.W., and Bergmeier S.C. In: Padwa A. (Ed). Comprehensive Heterocyclic Chemistry II Vol. 1A (1996), Pergamon, New York, NY p 1
3. Osborn H.M.I., and Sweeney J.B. Tetrahedron: Asymmetry 8 (1997) 1693
4. McCoull W., and Davis F.A. Synthesis (2000) 1347
5. Zwanenburg B., and ten Holte P. In: Metz P. (Ed). Stereoselective Heterocyclic Chemistry III (2001), Springer, Berlin 93-124
6. Sweeney J.B. Chem. Soc. Rev. 31 (2002) 247
7. Hu X.E. Tetrahedron 60 (2004) 2701
8. Lee W.-K., and Ha H.-J. Aldrichim. Acta 36 (2003) 57
9. D'hooghe M., Van Speybroeck V., Waroquierb M., and De Kimpe N. Chem. Commun. (2006) 1554
10. Kim M.S., Kim Y.-W., Hahm H.S., Jang J.W., Lee W.K., and Ha H.-J. Chem. Commun. (2005) 3062
11. Ma S.-h., Yoon D.-H., Ha H.-J., and Lee W.K. Tetrahedron Lett. 48 (2007) 269 and references are cited therein
12. 4 yielded the same (2S)-aminomethylaziridine from the commercially available (S)-1-[(R)-α-methylbenzyl]-2-aziridinecarboxamide.
13. D'hooghe M., and De kimpe N. Synlett (2004) 271
14. Schwan A.L., and Refvik M.D. Tetrahedron Lett. 34 (1993) 4901
15. ® 04.
16. Bergmeier S.C., and Seth P.P. J. Org. Chem. 62 (1997) 2671
17. Sweeny J.B., and Cantrill A.A. Tetrahedron 59 (2003) 3677
18. Bergmeier S.C., Fundy S.L., and Seth P.P. Tetrahedron 55 (1999) 8025
19. Kim Y., Ha H.-J., Han K.S., Ko S.H., Yun H., Chang J.W., Kim M.S., and Lee W.K. Tetrahedron Lett. 46 (2005) 4407
20. Fenster P.E., and Comess K.A. Pharmacotherapy 6 (1986) 1
21. Rudel R., and Lehmann-Horn F. Physiol. Rev. 65 (1985) 310
22. Kalso E., Tramer M.R., McQuay H.J., and Moore R.A. Eur. J. Pain 2 (1998) 3
23. Franchini C., Cellucci C., Corbo F., Lentini G., Scilimati A., Tortorella V., and Stasi F. Chirality 6 (1994) 590
24. Aav R., Parve O., Pehk T., Claesson A., and Martin I. Tetrahedron: Asymmetry 10 (1999) 3033
25. Carocci A., Catalano A., Corbo F., Duranti A., Amoroso R., Franchini C., Lentinia G., and Tortorella V. Tetrahedron: Asymmetry 11 (2000) 3619
26. Carocci A., Franchini C., Lentini G., Loiodice F., and Tortorella V. Chirality 12 (2000) 103
27. Yun J.M., Sin T.B., Hahm H.S., Lee W.K., and Ha H.-J. J. Org. Chem. 68 (2003) 7675