Ruthenium-Catalyzed Asymmetric Allylic Alkylation of Isatins
Barry M. Trost, Christopher A. Kalnmals, Divya Ramakrishnan, Michael C. Ryan, Rebecca W. Smaha, Sean Parkin
Abstract
A new ruthenium-based catalytic system for branched-selective asymmetric allylic alkylation is disclosed and applied to the synthesis of chiral isatin derivatives. The catalyst, which is generated in situ from commercially available CpRu(MeCN)3PF6 and a BINOL-derived phosphoramidite, is both highly active (TON up to 180) and insensitive to air and moisture. Additionally, the N-alkylated isatins accessible using this methodology are versatile building blocks that are readily transformed into chiral analogs of achiral drug molecules.
Topics & Concepts
ChemistryRutheniumTsuji–Trost reactionAlkylationCatalysisPhosphoramiditeCombinatorial chemistryAllylic rearrangementIsatinMoleculeOrganic chemistryDNAOligonucleotideBiochemistryAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods