A general and convenient synthetic method of geometrically pure (Z)-1-bromo-1-alkenes

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6759-6762

  Uenishi, Jun'ichi ^a   Kawahama, Reiko ^a   Shiga, Yasuhiko ^a   Yonemitsu, Osamu ^a   Tsuji, Jiro ^b  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^b KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ORGANOBROMINE DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0030576985     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01461-X     Document Type: Article

References (21)

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11. 2 are also suitable for the hydrogenolysis.
12. 7. For (E)-and (Z)-β-bromostyrenes; see Miller, R. B.; McGarvey, G. J. Org. Chem. 1978, 43, 4424-4431.
13. 8. (a)Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
14. (b) Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745-1747.
15. 3SnH (1.1 mmol) in anhydrous benzene (3 mL) under Ar atomosphere. After the mixture was stirred for 15 to 60 min at room temperature, an extractive work up with hexane or benzene and a purification by alumina column chromatography gave 2.
16. 10. The stereochemistries of all the products were confirmed by comparison with previous data reported in the literature, or determined by a coupling constants of the olefinic protons in proton nmr spectra.
17. 11. Roush, W. R.; Moriarty, K. J.; Brown, B. B. Tetrahderon Lett. 1990, 31, 6509-6512.
18. 12. Minato, A.; Suzuki, K.; Tamao, K. J. Am. Chem. Soc. 1987,109, 1257-1258.
19. 13. For example, the reaction of 1a and 1i gave a1 : 1 mixture of (E)-and (Z)-bromoalkenes along with a mixture of other complex products.
20. 14. The desired alkenes were obtained in 35∼-37% yields, although these authors succeeded in stereospecific hydrogenolysis of 1-iodo-1-alkenes with tributyltin hydride using a slow addition technique. See, Taniguchi, M.;Takeyama, Y.; Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2593-2595.
21. 2 (0.5 eq), and an additonal equivalent for the hydrogenolysis.