Titanocene- and zirconocene-mediated cyclization of allyl propargyl ethers. Stereoselective synthesis of 3-methylenetetrahydrofurans

Tetrahedron Letters

Volumn 37, Issue 50, 1996, Pages 9059-9062

  Miura, Katsukiyo ^a   Funatsu, Masashi ^a   Saito, Hiroshi ^a   Ito, Hajime ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

REAGENT; TETRAHYDROFURAN DERIVATIVE; TITANOCENE; ZIRCONIUM;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030577472     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02128-4     Document Type: Article

References (31)

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7. 2/EtMgBr:
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25. 2Zr-mediated cyclization of dienes containing an aryl allyl ether to chromans has been reported . Bird, A. J.; Taylor, R. J. K.; Wei, X. Synlett, 1995, 1237-1238.
26. 2 (0.55 mmol), Mg powder (1.1 mmol) activated by 1,2-dibromoethane (0.10 mmol), THF (5 ml). Substrate, M, yield (%): 5, Ti, 67; 5, Zr, 75; 6, Ti, 83; 6, Zr, 84. We also attempted the cyclization of diallyl ethers using the present method, but it resulted in failure because of the fast reductive cleavage of the C-O bonds of the substrates.
27. 2/Mg system, the concentration of reactants, that is the volume of THF, depended on the efficiency of the cyclization. The use of 5 ml of THF per 1 mmol of 1a resulted in 65% yield of 2a owing to the reductive cleavage of the C-O bond.
28. 11. Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 4912-4913.
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31. 3c