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Selective Synthesis of Ketones and Chiral Allylic Alcohols from the Addition of Arylboronic Acids to α,β-Unsaturated Aldehydes Mediated by a Transition Metal/Monophosphorus Ligand System

Rui Miao, Jinyong Huang, Yanping Xia, YiFei Wei, Renshi Luo* and Lu Ouyang*

*School of Pharmacy, Gannan Medical University, Ganzhou 341000, Jiangxi Province, P. R. China, Email: luorenshi2010163.com, oyl3074163.com

R. Miao, J. Huang, Y. Xia, Y. Wei, R. Luo, L. Ouyang, J. Org. Chem., 2022, 87, 8576-8588.

DOI: 10.1021/acs.joc.2c00703


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Abstract

A transition metal-mediated/monophosphorus ligand system enables the selective synthesis of ketones or chiral allylic alcohols in high yields/enantiomeric excess from the 1,2-addition of arylboronic acids to α,β-unsaturated aldehydes. While a Ru/monophosphorus system provides chiral allylic alcohols, the rhodium-catalyzed reaction provides ketones.

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proposed mechanism



Key Words

benzylic alcohols, allylic alcohols


ID: J42-Y2022