Towards Enantioselective Nucleophilic Trifluoromethylation

Various trifluoroacetamides and trifluoromethanesulfinamides, derived from chiral silylated amino alcohols, have been synthesized with the goal of achieving enantioselective nucleophilic trifluoromethylation. The best results were obtained with (R)‐phenylglycinol derivatives, but the ee values did n...

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Bibliographic Details
Published in:Chemistry : a European journal 2005-01, Vol.11 (3), p.939-944
Main Authors: Roussel, Solveig, Billard, Thierry, Langlois, Bernard R., Saint-James, Laurent
Format: Article
Language:English
Subjects:
amino alcohols
enantioselectivity
fluorination
nucleophilic addition
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Summary:Various trifluoroacetamides and trifluoromethanesulfinamides, derived from chiral silylated amino alcohols, have been synthesized with the goal of achieving enantioselective nucleophilic trifluoromethylation. The best results were obtained with (R)‐phenylglycinol derivatives, but the ee values did not exceed 30 %. Une grande variété de trifluoroacétamides et de trifluorométhanesulfinamides, dérivés d′aminoalcools silylés chiraux, a été synthétisée afin de réaliser des trifluorométhylations anioniques énantiosélectives. Les meilleurs résultats ont été obtenus à partir de dérivés du (R)‐phénylglycinol mais les excès énantiomériques n′excèdent pas 30 %. Enantioselective trifluoromethylation: Chiral trifluoroacetamides and trifluoromethanesulfinamides, derived from amino alcohols, have been synthesized to provide potential chiral nucleophilic trifluoromethylating reagents (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200400777