Ligand controlled highly regio- and enantioselective synthesis of alpha-acyloxyketones by palladium-catalyzed allylic alkylation of 1,2-enediol carbonates.

Journal of the American Chemical Society
Barry M TrostThomas Schmidt

Abstract

The palladium catalyzed decarboxylative asymmetric allylic alkylation of allyl 1,2-enediol carbonates 1 can decompose to either alpha-hydroxyketones 3 or alpha-hydroxyaldehydes 4. The product distribution is largely controlled by the ligand. Using Lnaph in DME we exclusively obtained the ketone product in good to excellent yields and high enantiomeric excesses. The reaction proceeds under extremely mild conditions, so we can have a broad range of choices of OR. Besides the commonly used protection groups such as OAc and OPiv, a more functionalized group such as methyl but-2-enoyl group can also be used, downstream process of which can afford other synthetically interesting structures.

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Citations

Jan 18, 2011·Chemical Reviews·Jimmie D WeaverJon A Tunge
Sep 30, 2010·Journal of the American Chemical Society·Rui ShangLei Liu
Nov 20, 2013·Journal of the American Chemical Society·Barry M TrostAndré P Dieskau
Aug 4, 2009·Journal of the American Chemical Society·Barry M Trost, David A Thaisrivongs
May 29, 2013·The Journal of Organic Chemistry·Wei XuBoris J Nachtsheim
Jul 23, 2011·Organic Letters·Vilius FranckevičiusRichard J K Taylor
Aug 23, 2016·Journal of the American Chemical Society·Xiaohong HuoWanbin Zhang
May 13, 2017·Angewandte Chemie·Rafael CanoGerard P McGlacken
Dec 6, 2018·Organic & Biomolecular Chemistry·Pragati K PrasadSudalai Arumugam
Sep 22, 2020·ChemistryOpen·Lukas Junk, Uli Kazmaier
Jun 20, 2013·Angewandte Chemie·Peng Zhang, Christian Wolf
Mar 24, 2009·Organic Letters·Xue Long Hou, Bao Hui Zheng
Jul 27, 2021·Chemical Reviews·Timothy B Wright, P Andrew Evans
Jun 11, 2014·The Journal of Organic Chemistry·Wengui WangYong Guo

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