手性硅氧基丙二烯对取代茚满酮的对映选择性合成。

Enantioselective synthesis of substituted indanones from silyloxyallenes.

机构信息

Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Silverman Hall, Evanston, Illinois 60208, USA.

出版信息

J Am Chem Soc. 2010 Feb 10;132(5):1472-3. doi: 10.1021/ja909669e.

DOI:10.1021/ja909669e

PMID:20085317

Abstract

A new approach for the synthesis of enantioenriched indanones by asymmetric carbonyl-ene/intramolecular Heck cyclization from racemic silyloxyallenes has been developed. The modular procedure affords highly substituted indenes and indanones with excellent chirality transfer from the optically active carbinols. Full transfer of stereochemical information is achieved in the presence of 1,2,2,6,6-pentamethylpiperidine and PdCl(2)(PPh(3))(2) (1 mol %) in DMF under microwave heating. Short reaction times and high yields have been demonstrated on a variety of substrates.

摘要

一种通过不对称羰基-烯/分子内 Heck 环化从外消旋硅氧基烯合成对映体富集的茚酮的新方法已经开发出来。该模块化方法提供了高取代的茚和茚满，具有从光学活性仲醇中出色的手性转移。在 1,2,2,6,6-五甲基哌啶和 PdCl(2)(PPh(3))(2)(1 mol%)的存在下，在 DMF 中微波加热时，完全实现了立体化学信息的转移。在各种底物上都表现出了短的反应时间和高的产率。