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Chiral 4‐Phenyl‐2‐trifluoromethyloxazolidine: A High‐Performance Chiral Auxiliary for the Alkylation of Amides
Author(s) -
Tessier Arnaud,
Pytkowicz Julien,
Brigaud Thierry
Publication year - 2006
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.200600738
Subject(s) - chiral auxiliary , alkylation , yield (engineering) , chemistry , amide , oxazolidine , cleavage (geology) , organic chemistry , combinatorial chemistry , stereochemistry , enantioselective synthesis , catalysis , physics , materials science , thermodynamics , fracture (geology) , composite material
A bit on the side : Extremely high diastereoselectivities (>99 % de ) were attained in the α‐alkylation and ‐allylation of amides by using a trifluoromethylated (sphere) oxazolidine as a chiral auxiliary. Reductive cleavage of the amide bond led to the recovery of this fluorinated chiral auxiliary in high yield.