Regio- and Enantioselective Synthesis of Allylic Fluorides by Electrophilic Fluorodesilylation of Allyl Silanes

Regio- and Enantioselective Synthesis of Allylic Fluorides by Electrophilic Fluorodesilylation of Allyl Silanes

Enantiopure N‐fluorocinchona alkaloids promoted the electrophilic fluorodesilylation of allyl silanes in a conceptually new approach to the regio‐ and enantioselective formation of allylic fluorides (see scheme). Excellent conversions were observed in these reactions, which afforded the desired ally...

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Veröffentlicht in:Angewandte Chemie International Edition 2003-07, Vol.42 (28), p.3291-3294
Hauptverfasser: Greedy, Benjamin, Paris, Jean-Marc, Vidal, Thierry, Gouverneur, Véronique
Format: Artikel
Sprache:eng
Schlagworte:
allylic compounds
asymmetric synthesis
cinchona alkaloids
fluorides
silanes
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Zusammenfassung:Enantiopure N‐fluorocinchona alkaloids promoted the electrophilic fluorodesilylation of allyl silanes in a conceptually new approach to the regio‐ and enantioselective formation of allylic fluorides (see scheme). Excellent conversions were observed in these reactions, which afforded the desired allylic fluorides with up to 96 % ee.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351405