Enantioselective α-Amination of 1,3-Dicarbonyl Compounds Using Squaramide Derivatives as Hydrogen Bonding Catalysts

被引:226
作者
Konishi, Hideyuki [1 ]
Lam, Tin Yiu [1 ]
Malerich, Jeremiah P. [1 ]
Rawal, Viresh H. [1 ]
机构
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
基金
美国国家卫生研究院;
关键词
BETA-KETO-ESTERS; DIELS-ALDER REACTIONS; AMINO-ACIDS; ELECTROPHILIC AMINATION; ASYMMETRIC-SYNTHESIS; BIFUNCTIONAL ORGANOCATALYSTS; CARBONYL-COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; MICHAEL ADDITION; RECENT PROGRESS;
D O I
10.1021/ol1005104
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic enantioselective alpha-hydrazination of 1,3-dicarbonyl compounds with azodicarboxylates was investigated in the presence of our newly developed hydrogen bonding catalyst, squaramide 3j. High yields and high enantioselectivities were achieved with low catalyst loading under mild conditions.
引用
收藏
页码:2028 / 2031
页数:4
相关论文
共 55 条
[1]   Chirally aminated 2-naphthols-organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel-Crafts amination [J].
Brandes, S ;
Bella, M ;
Kjoersgaard, A ;
Jorgensen, KA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) :1147-1151
[2]   Recent progress on the stereoselective synthesis of acyclic quaternary α-amino acids [J].
Cativiela, Carlos ;
Diaz-de-Villegas, Maria D. .
TETRAHEDRON-ASYMMETRY, 2007, 18 (05) :569-623
[3]   Recent progress on the stereoselective synthesis of cyclic quaternary α-amino acids [J].
Cativiela, Carlos ;
Ordonez, Mario .
TETRAHEDRON-ASYMMETRY, 2009, 20 (01) :1-63
[4]   A new Bronsted acid derived from squaric acid and its application to Mukaiyama aldol and Michael reactions [J].
Cheon, Cheol Hong ;
Yamamoto, Hisashi .
TETRAHEDRON LETTERS, 2009, 50 (26) :3555-3558
[5]   Highly enantioselective electrophilic amination and michael addition of cyclic β-ketoesters induced by lanthanides and (S,S)-ip-pybox:: The mechanism [J].
Comelles, Josep ;
Pericas, Alex ;
Moreno-Manas, Marcial ;
Vallribera, Adelina ;
Drudis-Sole, Gali ;
Lledos, Agusti ;
Parella, Teodor ;
Roglans, Anna ;
Garcia-Granda, Santiago ;
Roces-Fernandez, Laura .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (06) :2077-2087
[6]  
Dembech P, 2000, CHEM-EUR J, V6, P1281, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1281::AID-CHEM1281>3.0.CO
[7]  
2-F
[8]   Small-molecule H-bond donors in asymmetric catalysis [J].
Doyle, Abigail G. ;
Jacobsen, Eric N. .
CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743
[9]   Proline-catalyzed asymmetric α-amination of aldehydes and ketones -: An astonishingly simple access to optically active α-hydrazino carbonyl compounds [J].
Duthaler, RO .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) :975-978
[10]   Electrophilic α-amination of carbonyl compounds [J].
Erdik, E .
TETRAHEDRON, 2004, 60 (40) :8747-8782