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通过酸介导消除α-羟基硼酸酯立体选择性地形成三取代乙烯基硼酸酯。

Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters.

作者信息

Guan Weiye, Michael Alicia K, McIntosh Melissa L, Koren-Selfridge Liza, Scott John P, Clark Timothy B

机构信息

Department of Chemistry and Biochemistry, University of San Diego , 5998 Alcala Park, San Diego, California 92110, United States.

出版信息

J Org Chem. 2014 Aug 1;79(15):7199-204. doi: 10.1021/jo500773t. Epub 2014 Jul 14.

DOI:10.1021/jo500773t
PMID:24915498
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4120978/
Abstract

The copper-catalyzed diboration of ketones followed by an acid-catalyzed elimination leads to the formation of 1,1-disubstituted and trisubstituted vinyl boronate esters with moderate to good yields and selectivity. Addition of tosic acid to the crude diboration products provides the corresponding vinyl boronate esters upon elimination. The trisubstituted vinyl boronate esters are formed as the (Z)-olefin isomer, which was established by subjecting the products to a Suzuki-Miyaura coupling reaction to obtain alkenes of known geometry.

摘要

酮的铜催化双硼化反应，随后进行酸催化消除反应，可中等至良好产率和选择性地生成1,1-二取代和三取代的乙烯基硼酸酯。向粗双硼化产物中加入对甲苯磺酸，经消除反应可得到相应的乙烯基硼酸酯。三取代乙烯基硼酸酯以（Z）-烯烃异构体形式生成，这是通过将产物进行铃木-宫浦偶联反应以获得已知几何结构的烯烃而确定的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cef6/4120978/591f31c3d726/jo-2014-00773t_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cef6/4120978/22ce07608993/jo-2014-00773t_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cef6/4120978/076ae02ce742/jo-2014-00773t_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cef6/4120978/7950e4928b9f/jo-2014-00773t_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cef6/4120978/591f31c3d726/jo-2014-00773t_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cef6/4120978/22ce07608993/jo-2014-00773t_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cef6/4120978/076ae02ce742/jo-2014-00773t_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cef6/4120978/7950e4928b9f/jo-2014-00773t_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cef6/4120978/591f31c3d726/jo-2014-00773t_0008.jpg

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