New pyridine N-oxides as chiral organocatalysts in the asymmetric allylation of aromatic aldehydes

被引：83

作者：

Malkov, Andrei V. ^{[1
]}

Westwater, Mary-Margaret ^{[1
]}

Gutnov, Andrey ^{[2
]}

Ramirez-Lopez, Pedro ^{[1
]}

Friscourt, Frederic ^{[1
]}

Kadlcikova, Aneta ^{[1
]}

Hodacova, Jana ^{[3
]}

Rankovic, Zoran ^{[4
]}

Kotora, Martin ^{[5
]}

Kocovsky, Pavel ^{[1
]}

机构：

[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

[2] Univ Rostock, Leibniz Inst Catalysis, D-18055 Rostock, Germany

[3] Inst Chem Technol, Dept Organ Chem, CR-16628 Prague 6, Czech Republic

[4] Schering Plough Corp, Dept Med Chem, Newhouse ML1 5SH, Scotland

[5] Charles Univ Prague, Dept Organ Chem, Prague 12840 2, Czech Republic

来源：

TETRAHEDRON | 2008年 / 64卷 / 49期

基金：

英国工程与自然科学研究理事会;

关键词：

Enantioselective allylation; Allylsilane; Organocatalysis; Asymmetric catalysis; Pyridine N-oxides;

D O I：

10.1016/j.tet.2008.08.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric allylation of aromatic aldehydes 1 with allyltrichlorosilane (2) can be catalyzed by new terpene-derived bipyridine N,N'-dioxides 12-15 and an axially chiral biisoquinoline dioxide 17b with good enantioselectivities. Dioxides have been found to be more reactive catalysts than their monooxide counterparts. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

引用

页码：11335 / 11348

页数：14

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