Gold-catalyzed rearrangement of propargylic tert-butyl carbonates
| Autor: | Andrea Buzas, Fabien Gagosz, Florin M. Istrate |
|---|---|
| Přispěvatelé: | Laboratoire de synthèse organique (DCSO), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2009 |
| Předmět: |
Tert butyl
Reaction conditions Cyclic compound Reaction mechanism 010405 organic chemistry Chemistry Organic Chemistry Cross reactions 010402 general chemistry 01 natural sciences Biochemistry Chemical synthesis Combinatorial chemistry 0104 chemical sciences Catalysis Drug Discovery Organic chemistry Stereoselectivity |
| Zdroj: | Tetrahedron Tetrahedron, Elsevier, 2009, 65 (9), pp.1889-1901. ⟨10.1016/j.tet.2008.11.108⟩ |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2008.11.108⟩ |
| Popis: | International audience; Diversely substituted 4-alkylidene-1,3-dioxolan-2-ones are efficiently synthesized by a gold(I)-catalyzed rearrangement of propargylic tert-butyl carbonates. The substrates are readily accessible and the transformation, which is performed under mild reaction conditions using a low loading of catalyst, allows the synthesis of cyclic carbonates, which would be less efficiently obtained using traditional methods. This procedure has also been applied to the stereoselective synthesis of (E)- or (Z)-4-halomethylene-1,3-dioxolan-2-ones, which proved to be suitable substrates for palladium-catalyzed cross-coupling reactions. © 2008 Elsevier Ltd. All rights reserved. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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