Kinetic resolution of diols and pyridyl alcohols by Cu(II)(borabox)-catalyzed acylation

Organic Letters
Clément MazetAndreas Pfaltz

Abstract

[reaction: see text] Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)-catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.

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Citations

Aug 27, 2015·Organic Letters·Hailong YangXumu Zhang
Nov 8, 2007·Angewandte Chemie·Sebastian Rendler, Martin Oestreich
Jul 12, 2008·Angewandte Chemie·Christian E MüllerPeter R Schreiner
Oct 1, 2009·Angewandte Chemie·Derek J SchipperKeith Fagnou
Jun 22, 2011·Angewandte Chemie·Christian E Müller, Peter R Schreiner
Mar 8, 2011·Chemistry : a European Journal·Axel Franzke, Andreas Pfaltz
Aug 9, 2008·Chemistry : a European Journal·Valentin KöhlerAndreas Pfaltz
May 21, 2008·Inorganic Chemistry·Suribabu JammiTharmalingam Punniyamurthy
Apr 22, 2009·Chemical Reviews·Gráinne C Hargaden, Patrick J Guiry
Apr 29, 2021·Organic & Biomolecular Chemistry·Arianna BrandoleseAndrew D Smith
Dec 2, 2014·Journal of the American Chemical Society·Xiao-Hui YangQi-Lin Zhou
Jul 24, 2013·The Journal of Organic Chemistry·Christian E MüllerPeter R Schreiner
Jan 31, 2012·The Journal of Organic Chemistry·Ximin LiVladimir B Birman
Nov 28, 2013·Organic Letters·C Liana Allen, Scott J Miller

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