Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis
Year: 2016
Type: article
Abstract: The preparation of all possible stereoisomers of a given chiral molecule bearing multiple stereocenters by a simple and unified method is a significant challenge in asymmetric catalysis. We report stereodivergent allylic substitutions with aryl acetic acid esters catalyzed synergistically by a metallacyclic iridium complex and benzotetramisole. Through permutations of the enantiomers of the two chiral catalysts, all four stereoisomers of the products bearing two adjacent stereocenters are accessible with high diastereoselectivity and enantioselectivity. The resulting chiral activated ester products can be converted readily to enantioenriched amides, unactivated esters, and carboxylic acids in a one-pot manner.
DOI: 10.1021/jacs.6b11692
Authors: Xingyu Jiang, Jason J. Beiger, John F. Hartwig
Institution: University of California, Berkeley
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: Amination and Etherification of Aryl Halides and Olefins, G143247125, Mechanism and Development of Catalysts for the Synthesis of Amines, Ethers, and S, PALLADIUM CATALYZED FORMATION OF ARYLAMINE AND ARYLETHER, A proposal for the purchase of a new Cu anode Microsource X-ray Diffractometer wi, The Silyl-Directed Borylation of Aliphatic C-H Bonds
OpenAlex ID: W2562270443