Iridium-Catalyzed Kinetic Asymmetric Transformations of Racemic Allylic Benzoates
Year: 2010
Type: article
Abstract: Versatile methods for iridium-catalyzed, kinetic asymmetric substitution of racemic, branched allylic esters are reported. These reactions occur with a variety of aliphatic, aryl, and heteroaryl allylic benzoates to form the corresponding allylic substitution products in high yields (74-96%) with good to excellent enantioselectivity (84-98% ee) with a scope that encompasses a range of anionic carbon and heteroatom nucleophiles. These kinetic asymmetric processes occur with distinct stereochemical courses for racemic aliphatic and aromatic allylic benzoates, and the high reactivity of branched allylic benzoates enables enantioselective allylic substitutions that are slow or poorly selective with linear allylic electrophiles.
DOI: 10.1021/ja103779e
Institution: University of Illinois Urbana-Champaign
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: Amination and Etherification of Aryl Halides and Olefins, G1921871789, G2223967233, G2225206983, Mechanism and Development of Catalysts for the Synthesis of Amines, Ethers, and S, PALLADIUM CATALYZED FORMATION OF ARYLAMINE AND ARYLETHER, Mechanism and Rational Development of Catalytic Carbon-Carbon Bond-Forming Reacti, Transition Metal-Catalyzed, Asymmetric Allylic Borylation and Silylation
OpenAlex ID: W2024442246