Abstract
This review describes the development of enantiomerically pure selenium reagents as electrophiles in stereoselective synthesis. It outlines the addition of selenium electrophiles to alkenes, which can be used as part of key reactions in various transformations. Different nucleophiles can be employed in the addition reactions including oxygen, nitrogen and carbon nucleophiles. Furthermore, it has been shown that selenocyclisations can been performed using similar nucleophiles for the formation of different heterocycles. It has been established that the structure of the selenium electrophile, its counterion and the solvent all influence the course of these reactions. Most transformations use stoichiometric amounts of selenium containing reagents. Recently, selenenylation - deselenenylation reactions were discovered where only catalytic amounts of reagents are necessary.
Keywords: selenenylation reactions, nucleophiles, oximes, Catalytic Reactions, peroxodisulfates
Current Organic Chemistry
Title: New Developments with Chiral Electrophilic Selenium Reagents
Volume: 10 Issue: 15
Author(s): Danielle M. Browne and Thomas Wirth
Affiliation:
Keywords: selenenylation reactions, nucleophiles, oximes, Catalytic Reactions, peroxodisulfates
Abstract: This review describes the development of enantiomerically pure selenium reagents as electrophiles in stereoselective synthesis. It outlines the addition of selenium electrophiles to alkenes, which can be used as part of key reactions in various transformations. Different nucleophiles can be employed in the addition reactions including oxygen, nitrogen and carbon nucleophiles. Furthermore, it has been shown that selenocyclisations can been performed using similar nucleophiles for the formation of different heterocycles. It has been established that the structure of the selenium electrophile, its counterion and the solvent all influence the course of these reactions. Most transformations use stoichiometric amounts of selenium containing reagents. Recently, selenenylation - deselenenylation reactions were discovered where only catalytic amounts of reagents are necessary.
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Cite this article as:
Browne M. Danielle and Wirth Thomas, New Developments with Chiral Electrophilic Selenium Reagents, Current Organic Chemistry 2006; 10 (15) . https://dx.doi.org/10.2174/138527206778521213
DOI https://dx.doi.org/10.2174/138527206778521213 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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