Chiral 4-phenyl-2-trifluoromethyloxazolidine: A high-performance chiral auxiliary for the alkylation of amides

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Abstract

(Chemical Equation Presented) 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. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

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Tessier, A., Pytkowicz, J., & Brigaud, T. (2006). Chiral 4-phenyl-2-trifluoromethyloxazolidine: A high-performance chiral auxiliary for the alkylation of amides. Angewandte Chemie - International Edition, 45(22), 3677–3681. https://doi.org/10.1002/anie.200600738

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