The functionalization of alkenes with selenium compounds offers attractive possibilities for synthetic organic chemistry. Selenium electrophiles are quite powerful and can easily react with double bonds to generate the corresponding addition products after reaction with a nucleophile.
Thomas Wirth, Cardiff University, UK, and colleagues describe new chiral diselenides prepared from readily available, cheap starting materials in a very short synthesis and the addition reactions of their corresponding selenium electrophiles to alkenes.
The starting material for the one-step synthesis is bis(2-hydroxyphenyl) diselenide (6), which is easily prepared from
2-bromophenol (5). A subsequent Mitsunobu reaction can be successfully used with different chiral alcohols 7 under
very mild conditions to generate the required diselenides 8 in high yields.
The selenium electrophiles have been successfully applied in methoxyselenenylation reactions with good yields and diastereomeric ratios.
Image: (c) Wiley-VCH
Article Views: 2810
Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.