Regio- and stereoselective synthesis of (E)-1-alkylseleno-1,4-pentadienes by cross-coupling of allyl bromide with alkylselenovinylcoppers from alkylselenovinyldialkylboranes

Synthetic Communications

Volumn 26, Issue 23, 1996, Pages 4369-4373

  Yang, De Yu ^a   Huang, Xian ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ORGANOSELENIUM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029830211     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003839     Document Type: Article

References (11)

1. a) Brown, H. C. "Organic Synthesis via Boranes," wiley Interscience: New York, 1975.
2. b) Crag, G. M. L. "Organoboranes in Organic Synthesis," Marcel Dekker: New York, 1973.
3. c) Brown, H. C. and Basawaiah, O. J. Org. Chem. 1983, 48, 5080.
4. Tucker, C. E.; Davidson, J. E. and Knochel, P, J. Org. Chem. 1992, 57, 3482.
5. a) Hoshi, M.; Masuda, Y. and Arase, A. Bull. Chem. Soc. Jpn. 1990, 63, 447.
6. Hercsi, L.; Heimaus, B. and Allard, C. Tetrahedron Lett., 1994, 35, 6729.
7. Raucher, S.; Hansen, M. R.; Colter, M. A. J. Org. Chem. 1978, , 43, 4886.
8. 4. Removal of solvent under reduced pressure gave the terminal alkylselenoacetylene 1 which was purified by flash chromatography (light petroleum, bp30-60°C).
9. Brown, H. C.; Campbell, J. b. J.Org.Chem. , 1980, 45, 552.
10. Zweifel, G.; Arzoumanian, H. and Whitney, C. C. J. am. Chem. Soc., 1967, 89, 3652.
11. brown, H. C.; Knights, E. and Scouten, C. J. Amer. Chem. Soc. , 1974, 96, 7765.