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Diastereoselective Synthesis of Trifluoromethylated γ-Butyrolactones via N-Heterocyclic Carbene-Catalyzed Conjugated Umpolung of α,β-Unsaturated Aldehydes

✍ Scribed by Keiichi Hirano; Isabel Piel; Frank Glorius

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
185 KB
Volume
350
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

The N‐heterocyclic carbene‐catalyzed conjugate umpolung of differently substituted α,β‐unsaturated aldehydes is described. Coupling of these compounds with a variety of trifluoromethylated ketones results in the selective formation of fluorinated γ‐butyrolactones. Using thiazolium‐derived N‐heterocyclic carbenes, the unlike stereoisomers are formed predominantly, whereas the imidazol‐2‐ylidene IMes results in lower selectivities and the preferred formation of the like isomer.

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ChemInform Abstract: Diastereoselective
ChemInform Abstract: Diastereoselective Synthesis of Trifluoromethylated γ-Butyrolactones via N-Heterocyclic Carbene-Catalyzed Conjugated Umpolung of α,β-Unsaturated Aldehydes.
✍ Keiichi Hirano; Isabel Piel; Frank Glorius 📂 Article 📅 2008 🏛 John Wiley and Sons ⚖ 49 KB 👁 1 views

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