Abstract
Stereoselective synthesis of new C-C bonds is one of the main objectives of organic chemistry. In this field, silyl activation of alkenes is a useful organic tool in a huge number of Lewis acid promoted reactions due to the ability of the silicon to stabilize neighboring cations. This review summarizes the Lewis acid promoted addition of silyl enol ethers and allylsilanes to epoxides and other small oxygenated rings, which has proved to be an efficient method of synthesis of asymmetric alcohols and other target compounds.
Keywords: Alcohol, allylsilane, allylsiloxane, biomimetic cyclization, bishomoallylic alcohol, lactone, oxetane, oxirane, γ-hydroxyketone, propargylsilane.
Current Organic Chemistry
Title:Addition of Allylsilanes and Silyl Enol Ethers to Small Oxygenated Rings: New Tools for Organic Synthesis
Volume: 18 Issue: 5
Author(s): Carmen Hernandez-Cervantes, Miriam Alvarez-Corral, Manuel Munoz-Dorado and Ignacio Rodriguez-Garcia
Affiliation:
Keywords: Alcohol, allylsilane, allylsiloxane, biomimetic cyclization, bishomoallylic alcohol, lactone, oxetane, oxirane, γ-hydroxyketone, propargylsilane.
Abstract: Stereoselective synthesis of new C-C bonds is one of the main objectives of organic chemistry. In this field, silyl activation of alkenes is a useful organic tool in a huge number of Lewis acid promoted reactions due to the ability of the silicon to stabilize neighboring cations. This review summarizes the Lewis acid promoted addition of silyl enol ethers and allylsilanes to epoxides and other small oxygenated rings, which has proved to be an efficient method of synthesis of asymmetric alcohols and other target compounds.
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Cite this article as:
Hernandez-Cervantes Carmen, Alvarez-Corral Miriam, Munoz-Dorado Manuel and Rodriguez-Garcia Ignacio, Addition of Allylsilanes and Silyl Enol Ethers to Small Oxygenated Rings: New Tools for Organic Synthesis, Current Organic Chemistry 2014; 18 (5) . https://dx.doi.org/10.2174/1385272819666140201002221
DOI https://dx.doi.org/10.2174/1385272819666140201002221 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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