Synthesis of nitrogen heterocycles by intramolecular Michael type of amination via reduction of imines with di-n-butyliodotin hydride (n-Bu2SnIH)

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1579-1581

  Suwa, Toshihiro ^a   Shibata, Ikuya ^a   Nishino, Keita ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

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Indexed keywords

EID: 0000222417     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990225i     Document Type: Article

References (18)

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2. Glanzmann, M.; Karalai, C.; Ostersehlt, B.; Shoen, U.; Frese, C.; Winterfeldt, E. Tetrahedron Lett. 1982, 38, 2805.
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7. Imine reduction, for example: (a) Hutchins, R. O.; Hutchins, M. K. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 8, p 25.
8. (b) Lane, C. F. Synthesis 1975, 135.
9. (c) Gribble, G. W. Chem. Soc. Rev. 1998, 27, 395.
10. Tin hydride reduction, review. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987.
11. (a) Kawakami, T.; Miyatake, M.; Shibata, I.; Baba, A.; Matsuda, H. J. Org. Chem. 1996, 61, 376.
12. (b) Kawakami, T.; Sugimoto, T.; Shibata, I.; Baba, A.; Matsuda, H.; N. Sonoda, J. Org. Chem. 1995, 60, 2677.
13. (c) Shibata, I.; Moriuchi-Kawakami, T.; Tanizawa, D.; Suwa, T.; Sugiyama, E.; Matsuda H.; Baba, A. J. Org. Chem. 1998, 63, 383.
14. (d) Shibata, I.; Suwa, T.; Sugiyama, E.; Baba, A. Synlett 1998, 1081.
15. Sawer, A. K.; Brown, J. E.; Hanson, E. L. J. Organomet. Chem. 1965, 3, 464.
16. 2, 0.5 mmol) in THF (1 mL) at room temperature. To the solution were added substrate S (1 mmol) and aniline 6 (1 mmol). After the mixture was stirred at 0°C for 2 h, MeOH was added, and volatiles were removed under reduced pressure. The residue was chromatographed on silica gel (hexane/EtOAc = 3/1) to afford 8a.
17. Although the possibility of the attack of a free amine to enone is not excluded, we think that the more nucleophilic tin amide may play an important role in the cyclization.
18. 2SnIH works rather well for the formation of an iminium ion.