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Full Paper
Stereoselective Synthesis of Polysubstituted Tetrahydropyrans by Radical Cyclization of Epoxides using a Transition-Metal Radical Source
Article first published online: 26 AUG 2005
DOI: 10.1002/ejoc.200500424
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Banerjee, B. and Roy, S. C. (2006), Stereoselective Synthesis of Polysubstituted Tetrahydropyrans by Radical Cyclization of Epoxides using a Transition-Metal Radical Source. Eur. J. Org. Chem., 2006: 489–497. doi: 10.1002/ejoc.200500424
Publication History
- Issue published online: 2 JAN 2006
- Article first published online: 26 AUG 2005
- Manuscript Received: 10 JUN 2005
Keywords:
- Tetrahydropyrans;
- Radical cyclization;
- Epoxides;
- Transition metals
Abstract
Epoxyalkyl propargyl ethers 3a–f and allyl epoxyalkyl ethers 6a–c smoothly undergo radical cyclization reactions using a titanium(III) species (Cp2TiCl) as the radical initiator to form polysubstituted tetrahydropyrans 4a–f and 7a–c in good yields and with high diastreoselectivity. The titanium(III) species was prepared in situ from commercially available titanocene dichloride and Zn dust in THF. On the other hand, the epoxyalkyl propargyl ethers 3g and 3h furnished the spirocyclic ethers 4g and 4h, respectively, on radical cyclization reaction as the sole products. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)