论文信息 - Silicon-assisted ring opening of donor-acceptor substituted cyclopropanes. An expedient entry to substituted dihydrofurans.

Silicon-assisted ring opening of donor-acceptor substituted cyclopropanes. An expedient entry to substituted dihydrofurans.

[reaction: see text]. (tert-butyldiphenylsilyl)methylcyclopropanes undergo ring opening to furnish substituted dihydrofurans in good to excellent yields on treatment with TiCl4 in dichoromethane. The silicon that assists the regioselective ring opening is retained in the product to allow further functional group manipulations.

R. Balamurugan | V. Yadav

[1] G. Righi,et al. An easy approach to dihydrofurans by one-step cyclisation of 2-alkenyl substituted 1,3-dicarbonyl compounds , 2000 .

[2] V. Dragan,et al. Sakurai Addition and Ring Annulation of Allylsilanes with α,β-Unsaturated Esters. Experimental Results and ab Initio Theoretical Predictions Examining Allylsilane Reactivity , 2000 .

[3] H. Knölker,et al. Cycloadditions of Allylsilanes, Part 11. Stereoselective Synthesis of Hydroxycyclopentanes and Hydroxymethylcyclobutanes by Titanium Tetrachloride-Promoted [3+2] and [2+2] Cycloadditions of Sterically Hindered Allylsilanes and Subsequent Oxidative Cleavage of the Carbon-Silicon Bond , 1998 .

[4] I. Ryu,et al. One-pot conversions of (silylmethyl)cyclopropanes to homoallylic alcohols and 1,4-diols based on haloborane-induced ring opening , 1990 .

[5] T. Hirao,et al. Selective ring transformations of 1-[2-(trimethylsilylmethyl)cyclopropylcarbonyl]imidazoles , 1986 .

[6] M. E. Alonso,et al. STUDIES ON THE ORIGIN OF DIHYDROFURANS FROM α-DIAZOCARBONYL COMPOUNDS. CONCERTED 1,3-DIPOLAR CYCLOADDITION VS. NONSYNCHRONOUS COUPLING IN THE COPPER CHELATE CATALYZED REACTIONS OF α-DIAZODICARBONYL COMPOUNDS WITH ELECTRON-RICH OLEFINS , 1983 .