NaH-mediated iodoaziridination reaction of N-allylic tosylamides

Tetrahedron Letters

Volumn 38, Issue 48, 1997, Pages 8371-8374

  Kitagawa, Osamu ^a   Suzuki, Takashi ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

TOLUENESULFONAMIDE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; IODINATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0030703149     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10271-4     Document Type: Article

References (22)

1. (a) Bartlett, P. A. "Asymmetric Synthesis", Ed. Morrison, J. D. Academic Press, Orland, 1984, Vol 3, Part B, p411.
2. (b) Gardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321-3408.
3. Examples of haloepoxidation reactions of allyl alcohol derivatives which proceed via an ionic mechanism: (a) Ganem, B. J. Am. Chem. Soc. 1976, 98, 858-859.
4. (b) Midland, M. M.; Halterman, R. J. Org. Chem. 1981, 46, 1227-1229.
5. (c) Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis 1988, 862-868.
6. Haloepoxides-forming reaction from allyl alcohol derivatives under radical conditions has been also reported, (a) Suginome, H.; Wang, J. B. J. Chem. Soc., Chem. Commun. 1990, 1629-1630.
7. (b) Galatsis, P.; Millan, S. D.; Tetrahedron Lett. 1991, 32, 7493-7496.
8. (c) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687-4690.
9. 4-mediated iodocarbocyclization reaction of alkenylmalonates: (a) Taguchi, T.; Kitagawa, O.; Inoue, T.; J. Syn. Org. Chem. Jpn. 1995, 53, 770-779.
10. (b) Kitagawa, O.; Inoue, T. Taguchi, T. Reviews on Heteroatom Chemistry 1996, 15, 243-262.
11. 4. (a) Kitagawa, O.; Fujita, M.; Li, F.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615-618.
12. (b) Fujita, M.; Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. in press.
13. (a) Kitagawa, O.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1992, 33, 2167-2170.
14. (b) Inoue, T. Kitagawa, O.; Ochiai, O.; Taguchi, T. Tetrahedron: Asymmetry 1995, 6, 691-692.
15. 2 and NaH. Beckwith, A. L.; Zozer, M. J. Tetrahedron Lett. 1992, 33, 4975-4978.
16. Examples of preparation of halomethylaziridines by other methods: (a) Gensler, W. J. J. Am. Chem. Soc. 1948, 70, 1843-1846.
17. (b) Gensler, W. J.; Brooks, B. A. J. Org. Chem. 1966, 31 568-575.
18. (c) Kimpe, N. D.; Smaele, D. D.; Sakonyi, Z. J. Org. Chem. 1997, 62, 2448-2452 and references cited therein.
19. Synthesis of pyrrolidine or piperidine derivatives through bromoaminocyclization of N-pentenyl or N-hexenyl tosylamides has been reported by Tamaru et al. Tamaru, Y.; Kawamura, S.; Bando, T.; Tanaka, K.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5491-5500.
20. 3) δ 2.3, 21.6, 36.1, 41.0, 128.2, 129.7, 134.4, 144.8.
21. Haloaziridine product could not be obtained by the combination of NaH and NBS or NIS.
22. The incomplete stereospecificity observed in the trans-elimination of stereochemically pure syn-or anti-2f by Zn may be due to the contribution of radical cleavage mechanism in some extent. Kimpe, N. D.; Jolie, R.; Smaele, D. D. J. Chem. Soc., Chem. Commun. 1994, 1221-1222.