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Bulky tertiary amines, especially dicyclohexylisobutylamine, smoothly reduced alpha,beta-unsaturated ketones in the presence of trichlorosilyl triflate to give the corresponding saturated ketones in excellent yields. Isotope-labeling studies revealed that an alpha-hydrogen of the amine was transferred to the enones during reduction.
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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate