Catalytic Asymmetric Allylic Substitution/Isomerization with Central Chirality Transposition
Zhengyu Han, Han Zhuang, Luning Tang, Yu Zang, Wengang Guo, Hai Huang, Jianwei Sun
Abstract
We have developed a catalytic asymmetric allylic substitution/isomerization process with central chirality transposition. This process takes advantage of the ambident reactivity of the 2-indole imine methide generated in situ from racemic tertiary indolylmethanols. The use of a suitable chiral phosphoric acid catalyst and an ortho-directing group allowed regioselective formation a C–C bond at the 3 position but enantiocontrolled construction of a stereogenic center at the 2-benzylic position.
Topics & Concepts
ChemistryIsomerizationAllylic rearrangementSubstitution (logic)CatalysisChirality (physics)Transposition (logic)StereochemistryOrganic chemistryChiral symmetry breakingQuantum mechanicsComputer scienceNambu–Jona-Lasinio modelPhilosophyQuarkLinguisticsPhysicsProgramming languageAsymmetric Synthesis and CatalysisAxial and Atropisomeric Chirality SynthesisAsymmetric Hydrogenation and Catalysis