Asymmetric Reaction of Organolithium Reagents Under Control of Chiral Ligand.

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  • キラル配位子制御による有機リチウム反応剤の不斉付加反応
  • キラル ハイイシ セイギョ ニ ヨル ユウキ リチウム ハンノウザイ ノ フセイ フカ ハンノウ

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Development of a new methodology for an asymmetric reaction of organolithium reagents constitutes fundamental progress in recent synthetic organic chemistry. The methodology we developed relies on an external chiral coordinating reagent which forms a chelated complex with organolithium reagents. Under the positive control of a chiral dimethyl ether of stilbenediol 8, an asymmetric conjugate addition reaction of organolithium reagents with unsaturated imines and esters proceeded successfully to afford the corresponding addition products in reasonably high stereoselectivity. The sense of stereochemistry is predictable based on a coordination model. The methodology has been extended to a catalytic asymmetric 1, 2-addition reaction of organolithium reagents with imines. Asymmetric Horner-Wadsworth-Emmons reaction of phosphonate with 4-substituted cyclohexanone and enantiotopic selective opening of cyclohexene oxide were also another successful application of the methodology.<BR>The methodology has been successfully applied to an asymmetric synthesis of biologically potent compounds. Dihydrexidine, promising anti-Parkinsonism candidate, and salsolidine, a representative isoquinoline alkaloid, have been synthesized using asymmetric addition reactions of organolithium reagents as the key steps.

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