Domino Asymmetric Conjugate Addition-Conjugate Addition

被引：31

作者：

Germain, Nicolas ^{[1
]}

Schlaefli, Doriane ^{[1
]}

Chellat, Mathieu ^{[1
]}

Rosset, Stephane ^{[1
]}

Alexakis, Alexandre ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 07期

基金：

瑞士国家科学基金会; 新加坡国家研究基金会;

关键词：

QUATERNARY STEREOGENIC CENTERS; ONE-POT; ENANTIOSELECTIVE SYNTHESIS; TANDEM REACTIONS; ENOL ETHERS; REAGENTS; SULFONES; ALPHA; CONVERSION; FURANS;

D O I：

10.1021/ol5005752

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioenriched Al-, Mg-, and Zn-enolates undergo electrophilic trapping by nitroolefins and vinylsulfones to afford 1,4-diketones and 2-(bis(phenylsulfonyl)ethyl)ketones in good yield and excellent diastereoselectivity. A one-pot preparation of indenes and enantiopure syntheses of tetrahydrobenzofurans, tetrahydrobenzopyrroles, and azulenes are disclosed. A site-selective two-step sequence of three conjugate additions is also demonstrated.

引用

页码：2006 / 2009

页数：4

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