Et3B-induced hydrogermylation of alkenes and silyl enol ethers

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1911-1914

  Tanaka, Shinobu ^a   Nakamura, Tomoaki ^a   Yorimitsu, Hideki ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001348074     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005977n     Document Type: Article

References (31)

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15. Hydrostannylation of alkenes via radical process, see: (a) Miura, K.; Saito, H.; Uchinokura, S.; Hosomi, A. Chem. Lett. 1999, 659.
16. (b) Hanessian, S.; Leger, R. J. Am. Chem. Soc. 1992, 114, 3115.
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18. For hydrosilylation of alkenes via radical process, see: Kopping, B.; Chatgilialoglu, C.; Zehnder, M.; Giese, B. J. Org. Chem. 1992, 57, 3994 and references therein.
19. Tri-2-furanylgermane was easily prepared according to the literature. Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1999, 1415.
20. 2 remaining in the reaction flask. Additional oxygen was not necessary.
21. 3: C, 62.07; H, 6.77. Found: C, 61.83; H, 6.77.
22. 2O, 80% and 8%. The best results were obtained without solvent.
23. 3SnH afforded the corresponding adduct in 82%, 94%, or <20% yield, respectively.
24. 3: C, 61.52; H, 5.98. Found: C, 61.77; H, 6.09.
25. The stereochemical outcome, which is tentative, might be explained by the steric hindrance of tri-2-furanylgermyl group. Tri-2-furanylgermane would approach the intermediary carbon radical from the opposite side of germyl moiety.
26. For a mechanistic discussion of the addition of germyl radicals to alkenes, see ref 3e.
27. (a) Ager, D. J. Org. React. 1990, 38, 1.
28. (b) Kelly, S. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 3.1, p 729.
29. Kawashima, T.; Iwama, N.; Tokitoh, N.; Okazaki, R. J. Org. Chem. 1994, 59, 491-493.
30. The major stereoisomer of 5a can be separated by silica gel column chromatography.
31. Shapiro, R. H. Org. React. 1976, 23, 405.