铜（II）（硼杂环）催化酰化对二醇和吡啶醇的动力学拆分

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

作者信息

Mazet Clément, Roseblade Stephen, Köhler Valentin, Pfaltz Andreas

机构信息

Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.

出版信息

Org Lett. 2006 Apr 27;8(9):1879-82. doi: 10.1021/ol060443t.

DOI:10.1021/ol060443t

PMID:16623574

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.

摘要

[反应：见正文] 硼桥连双恶唑啉（硼恶唑啉）配体已用于铜（II）催化的吡啶醇和1,2 - 二醇的苯甲酰化反应。使用硼恶唑啉和双恶唑啉（恶唑啉）配体均可实现1,2 - 二醇的高效动力学拆分。硼恶唑啉配体在合适的吡啶醇的苯甲酰化反应中诱导出高选择性，其表现优于双恶唑啉。此外，高度对映选择性的铜（II）（硼恶唑啉）催化的苯甲酰化反应已用于合成吡啶醇的两种对映体。