One-pot regio- and stereoselective cyclization of 1,2,n-triols |
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Authors: | Zheng Tao Narayan Radha S Schomaker Jennifer M Borhan Babak |
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Institution: | Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA. |
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Abstract: | A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry of the 1,2-diol is transferred to the product with complete fidelity (inversion at the site of cyclization), and the reaction proceeds with high regioselectivity. The process is akin to the Lewis acid-catalyzed intramolecular ring-opening of epoxides with hydroxyl groups yielding cyclic ethers of various sizes with regio- and stereochemical control. |
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