Premium
Regio‐ and Enantioselective Synthesis of Allylic Fluorides by Electrophilic Fluorodesilylation of Allyl Silanes
Author(s) -
Greedy Benjamin,
Paris JeanMarc,
Vidal Thierry,
Gouverneur Véronique
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351405
Subject(s) - allylic rearrangement , enantioselective synthesis , regioselectivity , enantiopure drug , chemistry , nucleophile , electrophile , silanes , electrophilic fluorination , organic chemistry , kinetic resolution , tsuji–trost reaction , reagent , combinatorial chemistry , catalysis , silane
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.