Stereoselective functionalization of cyclopropane derivatives using bromine/magnesium and sulfoxide/magnesium exchange reactions
| Autor: | Paul Knochel, Felix Kopp, Genia Sklute, Kurt Polborn, Ilan Marek |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Addition reaction
Bromine Magnesium Organic Chemistry chemistry.chemical_element Sulfoxide General Medicine Biochemistry Medicinal chemistry Cyclopropane law.invention chemistry.chemical_compound chemistry law Electrophile Surface modification Organic chemistry Stereoselectivity Physical and Theoretical Chemistry Walden inversion |
| Zdroj: | Organic letters. 7(17) |
| ISSN: | 1523-7060 |
| Popis: | The reaction of 2,2-dibromo-1-methyl-cyclopropanecarbonitrile (1) with i-PrMgCl in Et(2)O/CH(2)Cl(2) provides the cis-magnesium-carbenoid (2), which reacts with high retention of configuration with various electrophiles. If E = SPh, a stereoselective generation of a quaternary center via a sequential Br/Mg- and sulfoxide/Mg-exchange can be achieved. [reaction: see text] |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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