Synthesis of a novel ate tin hydride complex bearing a nuoleophilic iodide substituent and 1,4-regioselective reduction of α,β-unsaturated aldehydes

Organometallics

Volumn 18, Issue 20, 1999, Pages 3965-3967

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

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000611162     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990262d     Document Type: Article

References (31)

1. For example: (a) Davis. A. G. Organotin Chemistry; VCH: New York, 1997; p 236. (b) Harrison, P. G. Chemistry of Tin; Blackie: London, 1989; p 282.
2. For example: (a) Davis. A. G. Organotin Chemistry; VCH: New York, 1997; p 236. (b) Harrison, P. G. Chemistry of Tin; Blackie: London, 1989; p 282.
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16. -1.
17. For example: (a) Holecek, J.; Nádvorník, M.; Handlír, K.; Lycka, A. J. Organomet. Chem. 1983, 241, 177-184. (b) Nádvorník, M.; Holecek, J.; Handlír, K.; Lycka, A. J. Organomet. Chem. 1984, 275, 43-51.
18. For example: (a) Holecek, J.; Nádvorník, M.; Handlír, K.; Lycka, A. J. Organomet. Chem. 1983, 241, 177-184. (b) Nádvorník, M.; Holecek, J.; Handlír, K.; Lycka, A. J. Organomet. Chem. 1984, 275, 43-51.
19. 1H) = 2336 Hz.
20. To a THF solution of the tin ate complex I (1 mmol) prepared according to ref 8 was added 2,3-epoxypropylbenzene (1) (1 mmol), and the mixture was stirred at room temperature for 15 min. After quenching with MeOH (5 mL), volatiles were removed under reduced pressure. The residue was subjected to silica gel column chlomatgraphy, eluting with hexanes-EtOAc (9:1) to give the products 2 and 3. Further purification was performed by silica gel TLC eluting with hexanes-EtOAc (9:1).
21. - at room temperature for 15 min gave 3 in a quantitative yield.
22. Greeves, N. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 8, Chapter 1.1, pp 1-24.
23. (a) Keinan, E.; Gleize, P. A. Tetrahedron Lett. 1982, 23, 477-480.
24. (b) Sommovigo, M.; Alper, H. Tetrahedron Lett. 1993, 34, 59-62.
25. Grushin, V. V.; Alper, H. Organometallics 1991, 10, 831-833.
26. (a) Lipshutz, B. H.; Ung, C. S.; Sengupta, S. Synlett 1989, 64-65.
27. (b) Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1989, 30, 5677-5680.
28. Saito, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 2928-2929.
29. To a THF solution of the tin ate complex I (1.5 mmol) prepared according to ref 8 was added n-hexenal (4a) (2 mmol), and the mixutre was stirred at room temperature for 15 min. After quenching with MeOH (5 mL), volatiles were removed under reduced pressure. The residue was subjected to silica gel column chlomatgraphy, eluting with hexanes-EtOAc (9:1) to give the products 5a. Further purification was performed by silica gel TLC eluting with hexanes-EtOAc (9:1).
30. -.
31. - complex, it is assumed that the Sn-H bond occupies the axial position, increasing the hydridic character.