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• W2808820061 abstract "We herein present a facile and column-free synthetic route toward a structurally unique oxa-spirocyclic diphenol, termed as O-SPINOL. Features of the synthesis include the construction of the all-carbon quaternary center at an early stage, a key double intramolecular SNAr step to introduce the spirocycles and the feasibility of operating on >100 g scale. Both enantiomers of O-SPINOL can be easily accessed through optical resolution with l-proline by control of the solvent. The chiral tridentate ligand O-SpiroPAP derived from O-SPINOL has been successfully synthesized and applied in the iridium-catalyzed asymmetric hydrogenation of bridged biaryl lactones under mild reaction conditions, providing valuable and enantioenriched axially chiral molecules in excellent yields and enantioselectivities (up to 99% yield and >99% ee). This method represents a rare example of constructing axially chiral molecules by direct reduction of esters with H2." @default.
• W2808820061 created "2018-06-29" @default.
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• W2808820061 date "2018-06-19" @default.
• W2808820061 modified "2023-10-14" @default.
• W2808820061 title "Design and Synthesis of Chiral <i>oxa</i>-Spirocyclic Ligands for Ir-Catalyzed Direct Asymmetric Reduction of Bringmann’s Lactones with Molecular H₂" @default.
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• W2808820061 doi "https://doi.org/10.1021/jacs.8b03642" @default.
• W2808820061 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/29920089" @default.
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