6533b7dcfe1ef96bd12729b7
RESEARCH PRODUCT
N1-Functionalized Indole-Phosphane Oxazoline (IndPHOX) Ligands in Asymmetric Allylic Substitution Reactions
Robert FranzénYu WangKari RissanenMatti J. P. Vaismaasubject
Substitution reactionAllylic rearrangementChemistryorganic chemicalsOrganic ChemistrySubstituentfood and beveragesOxazolineAlkylationAsymmetric inductionMedicinal chemistrychemistry.chemical_compoundTsuji–Trost reactionPhysical and Theoretical Chemistryta116Aminationdescription
N-Functionalized IndPHOX ligands bearing various groups have been synthesized and the effects of the N1-substituent on the reaction rate, yield, and asymmetric induction in a palladium-catalyzed allylic substitution reaction are reported. The presence of an oxygen atom in the ligands, namely an N-MOM or N-THP group, led to enhancement of the enantioselectivity in the allylic amination reaction. In addition, a ligand with a chiral oxazoline ring at C-1 and a phosphane substituent at C-2 provided high enantioselectivity in good yield in an asymmetric allylic alkylation reaction.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-01-25 | European Journal of Organic Chemistry |