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

共 50 条

[31] A NEW METHOD FOR DEOXYGENATION OF AROMATIC N-OXIDES
ABRAMOVI.R
ADAMS, KAH
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1961, 39 (10): : 2134 - &
[32] Asymmetric allylation of aromatic aldehydes catalyzed by chiral phosphoramides prepared from (S)-proline
Iseki, K
Kuroki, Y
Takahashi, M
Kishimoto, S
Kobayashi, Y
TETRAHEDRON, 1997, 53 (10) : 3513 - 3526
[33] PHOTOCHEMISTRY OF PYRIDINE N-OXIDES
LOHSE, C
HAGEDORN, L
ALBINI, A
FASANI, E
TETRAHEDRON, 1988, 44 (09) : 2591 - 2600
[34] Origin of Enantioselectivity in the Propargylation of Aromatic Aldehydes Catalyzed by Helical N-Oxides
Lu, Tongxiang
Zhu, Rongxiu
An, Yi
Wheeler, Steven E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (06) : 3095 - 3102
[35] REDUCTION OF PYRIDINE N-OXIDES
RAO, RP
AUSTRALIAN JOURNAL OF CHEMISTRY, 1964, 17 (12) : 1534 - &
[36] PHOTOCHEMISTRY OF AROMATIC N-OXIDES .11. EFFECTS OF COPPER-SALTS ON THE PHOTOCHEMISTRY OF MONOSUBSTITUTED PYRIDINE N-OXIDES
BELLAMY, F
STREITH, J
JOURNAL OF CHEMICAL RESEARCH-S, 1979, (01): : 18 - 19
[37] A new approach to axially chiral bipyridine N,N′-dioxides bearing aromatic substituents and their use for catalytic asymmetric allylation of aldehydes with allyl(trichloro)silane
Kina, A
Shimada, T
Hayashi, T
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) : 1169 - 1174
[38] Synthesis and Properties of New (Phosphinoylmethyl)Pyridine N-Oxides
Pailloux, Sylvie L.
Rosario-Amorin, Daniel
Chakravarty, Manab
Camus, Jean-Michel
Smith, Karen Ann
Duesler, Eileen N.
Dickie, Diane A.
Paine, Robert T.
Klausmeyer, Kevin K.
Padron, Daniel A.
Hay, Benjamin P.
Delmau, Laetitia H.
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2013, 639 (07): : 1101 - 1116
[39] A NEW DESOXYGENATION OF PYRIDINE AND ITS HOMOLOG N-OXIDES
SHIMIZU, M
DOHMORI, R
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1952, 72 (12): : 1643 - 1644
[40] PHOTOREACTIONS OF AROMATIC HETEROCYCLIC N-OXIDES .4. PHOTOCHEMISTRY OF PYRIDINE-OXIDES
STREITH, J
SIGWALT, C
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1970, (03): : 1157 - &

← 1 2 3 4 5 →