Trimethyl Orthoacetate and Ethylene Glycol Mono-Vinyl Ether as Enolate Surrogates in Enantioselective Iridium-Catalyzed Allylation

被引：31

作者：

Sempere, Yeshua ^{[1
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] Eidgenoss Tech Hsch Zurich, Lab Organ Chem, HCI H335, Vladimir Prelog Weg 3, CH-8093 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 26期

基金：

瑞士国家科学基金会;

关键词：

allylation; asymmetric catalysis; iridium; total synthesis; trimethyl orthoacetate; ASYMMETRIC ALLYLIC ALKYLATION; ALPHA-AMINO-ACIDS; SYNERGISTIC IRIDIUM; SUBSTITUTIONS; REGIO; ENANTIO; ALDEHYDES; DIASTEREO; ACETATES; ESTERS;

D O I：

10.1002/anie.201803558

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Trimethyl orthoacetate and ethylene glycol mono-vinyl ether are employed in iridium-catalyzed enantioselective allylation reactions. The method documented enables their convenient use as surrogates for silyl ketene acetals and silyl enol ethers to prepare gamma,delta-kunsaturated esters and protected aldehydes with excellent enantioselectivity. The utility of this novel method has been demonstrated by its implementation in a formal enantioselective synthesis of the meroterpenoid (+)-conicol.

引用

页码：7654 / 7658

页数：5

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