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

被引：62

作者：

Trost, Barry M. ^{[1
]}

Xu, Jiayi ^{[1
]}

Schmidt, Thomas ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 36期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1021/ja8038954

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The palladium catalyzed decarboxylative asymmetric allylic alkylation of allyl 1,2-enediol carbonates 1 can decompose to either α-hydroxyketones 3 or α-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. Copyright © 2008 American Chemical Society.

引用

页码：11852 / 11853

页数：2

共 36 条

[1] Synthesis of optically active α-hydroxy ketones by enantioselective oxidation of silyl enol ethers with a fructose-derived dioxirane [J].