Imine and iminium precursors as versatile intermediates in enantioselective organocatalysis

被引:65
作者
Kataja, Antti O. [1 ]
Masson, Geraldine [1 ,2 ]
机构
[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France
[2] Univ Amsterdam, NL-1012 WX Amsterdam, Netherlands
关键词
Asymmetric; Imine; Iminium; Surrogate; Precursor; Organocatalysis; CHIRAL PHOSPHORIC-ACID; FRIEDEL-CRAFTS REACTION; ASYMMETRIC MANNICH REACTION; GENERATED IN-SITU; DEHYDROGENATIVE COUPLING REACTIONS; N-ACYLIMINIUM IONS; AZA-HENRY REACTION; C-H BONDS; UNMODIFIED ALPHA; BETA-UNSATURATED ALDEHYDES; INTERMOLECULAR ADDITION-REACTIONS;
D O I
10.1016/j.tet.2014.06.101
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[No abstract available]
引用
收藏
页码:8783 / 8815
页数:33
相关论文
共 210 条
[1]   Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas [J].
Aillaud, Isabelle ;
Barber, David M. ;
Thompson, Amber L. ;
Dixon, Darren J. .
ORGANIC LETTERS, 2013, 15 (12) :2946-2949
[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]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[4]   Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts [J].
Alix, Aurelien ;
Lalli, Claudia ;
Retailleau, Pascal ;
Masson, Geraldine .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) :10389-10392
[5]   Bronsted Acid Catalyzed Enantioselective α-Amidoalkylation in the Synthesis of Isoindoloisoquinolines [J].
Aranzamendi, Eider ;
Sotomayor, Nuria ;
Lete, Esther .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (06) :2986-2991
[6]   Solventless clay-promoted Friedel-Crafts reaction of indoles with α-amido sulfones:: Unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles [J].
Ballini, Roberto ;
Palmieri, Alessandro ;
Petrini, Marino ;
Torregiani, Elisabetta .
ORGANIC LETTERS, 2006, 8 (18) :4093-4096
[7]   Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids [J].
Basle, Olivier ;
Li, Chao-Jun .
ORGANIC LETTERS, 2008, 10 (17) :3661-3663
[8]   Highly enantioselective organocatalytic formation of a quaternary carbon center via chiral Bronsted acid catalyzed self-coupling of enamides [J].
Baudequin, Christine ;
Zamfir, Alexandru ;
Tsogoeva, Svetlana B. .
CHEMICAL COMMUNICATIONS, 2008, (38) :4637-4639
[9]   Catalytic stereoselective benzylic C-H functionalizations by oxidative C-H activation and organocatalysis [J].
Benfatti, Fides ;
Capdevila, Montse Guiteras ;
Zoli, Luca ;
Benedetto, Elena ;
Cozzi, Pier Giorgio .
CHEMICAL COMMUNICATIONS, 2009, (39) :5919-5921
[10]  
Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/C3SC52265B, 10.1039/c3sc52265b]