Asymmetric Catalytic Meerwein–Ponndorf–Verley Reduction of Ketones with Aluminum(III)-VANOL Catalysts
Zheng Li, Xiaopeng Yin, Aliakbar Mohammadlou, Ryan P. Sullivan, Yong Guan, Richard J. Staples, William D. Wulff
Abstract
We report herein an efficient aluminum-catalyzed asymmetric MPV reduction of ketones with broad substrate scope and excellent yields and enantiomeric inductions. A variety of aromatic (both electron-poor and electron-rich) and aliphatic ketones were converted to chiral alcohols in good yields with high enantioselectivities (26 examples, 70–98% yield and 82–99% ee). This method operates under mild conditions (−10 °C) and low catalyst loading (1–5 mol %). Furthermore, this process is catalyzed by the earth-abundant main-group element aluminum and employs 2-propanol as the hydride source.
Topics & Concepts
CatalysisChemistryYield (engineering)EnantiomerSubstrate (aquarium)HydrideEnantiomeric excessOrganic chemistryCombinatorial chemistryEnantioselective synthesisHydrogenOceanographyGeologyMetallurgyMaterials scienceAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSurface Chemistry and Catalysis