Design of axially chiral dicarboxylic acid for asymmetric Mannich reaction of arylaldehyde N-Boc imines and diazo compounds

被引:211
作者
Hashimoto, Takuya [1 ]
Maruoka, Keiji [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan
关键词
D O I
10.1021/ja0713375
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
An axially chiral dicarboxylic acid has been prepared as a new class of chiral hydrogen-bonding catalysts and applied to the highly enantioselective Mannich reaction of arylaldehyde N-Boc imines and diazo compounds.
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收藏
页码:10054 / +
页数:3
相关论文
共 43 条
[1]
Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].
Akiyama, T ;
Morita, H ;
Itoh, J ;
Fuchibe, K .
ORGANIC LETTERS, 2005, 7 (13) :2583-2585
[2]
Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[3]
Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].
Akiyama, Takahiko ;
Morita, Hisashi ;
Fuchibe, Kohei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071
[4]
Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[5]
Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[6]
Protonated chiral catalysts: Versatile tools for asymmetric synthesis [J].
Bolm, C ;
Rantanen, T ;
Schiffers, I ;
Zani, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1758-1763
[7]
Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines [J].
Connon, Stephen J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3909-3912
[8]
Catalytic asymmetric allylation of aldehydes and related reactions with bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid [J].
Hanawa, H ;
Uraguchi, D ;
Konishi, S ;
Hashimoto, T ;
Maruoka, K .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (18) :4405-4413
[9]
Bis(((S)-binaphthoxy)(isopropoxy)titanium) oxide as a μ-oxo-type chiral Lewis acid:: Application to catalytic asymmetric allylation of aldehydes [J].
Hanawa, H ;
Hashimoto, T ;
Maruoka, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1708-1709
[10]
Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst [J].
Huang, Y ;
Unni, AK ;
Thadani, AN ;
Rawal, VH .
NATURE, 2003, 424 (6945) :146-146