Organocatalyzed synthesis of chiral non-racemic 1,4-dihydropyridazines

被引：23

作者：

Pitacco, Giuliana ^{[1
]}

Attanasi, Orazio A. ^{[2
]}

De Crescentini, Lucia ^{[2
]}

Favi, Gianfranco ^{[2
]}

Felluga, Fulvia ^{[1
]}

Forzato, Cristina ^{[1
]}

Mantellini, Fabio ^{[2
]}

Nitti, Patrizia ^{[1
]}

Valentin, Ennio ^{[1
]}

Zangrando, Ennio ^{[1
]}

机构：

[1] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy

[2] Univ Urbino, Ist Chim Organ, I-61029 Urbino, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 05期

关键词：

CATALYZED MICHAEL ADDITION; ASYMMETRIC MICHAEL; STRAIGHTFORWARD ENTRY; ALDOL REACTIONS; KETONES; ALDEHYDES; ACID; 1,2-DIAZA-1,3-BUTADIENES; AMINOCARBONYLAZOALKENES; NITROALKENES;

D O I：

10.1016/j.tetasy.2010.03.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral non-racemic 1,4-dihydropyridazines were prepared by the reaction of 1,2-diaza-1,3-dienes with arylacetaldehydes under organocatalytic conditions. L-Proline and (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine coupled with trifluoroacetic acid were used as organocatalysts. Enantiomeric excesses ranged from 25% to 78%. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：617 / 622

页数：6

共 50 条

[31] ASYMMETRIC SYNTHESES FROM CHIRAL NON-RACEMIC OXAZOLINES
MEYERS, AL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1974, : 34 - 34
[32] STUDIES ON THE ALKYLATION OF CHIRAL, NON-RACEMIC, TRICYCLIC PYRROLIDINONES
RAGAN, JA
CLAFFEY, MC
HETEROCYCLES, 1995, 41 (01) : 57 - 70
[33] Diastereoselective cycloadditions of chiral non-racemic azomethine imines
Roussi, F
Chauveau, A
Bonin, M
Micouin, L
Husson, HP
SYNTHESIS-STUTTGART, 2000, (08): : 1170 - 1179
[34] Synthesis of chiral, non-racemic cyclopentenones from allylic hydroxy phosphonates.
Spilling, CD
Yan, BL
Bandyopadhyay, S
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U367 - U368
[35] Efficient preparation of chiral non-racemic sulfur compounds
Minville, Joannie
Girardin, Melina
Spino, Claude
CANADIAN JOURNAL OF CHEMISTRY, 2007, 85 (09) : 603 - 618
[36] 1,4-Dihydropyridazines as inhibitors of free radical polymerization and gelation of styrene-divinyl benzene
Loy, Douglas
Bagge, Robb
Sun, Wenmo
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
[37] Solid-phase organic synthesis of chiral, non-racemic 1,2,4-trisubstituted 1,4-diazepanes with high σ1 receptor affinity
Fanter, Lena
Schepmann, Dirk
Wuensch, Bernhard
ARCHIV DER PHARMAZIE, 2018, 351 (01)
[38] Synthesis and electrospray mass spectrometric studies on a chiral, non-racemic, phosphoramide receptor molecule
Smith, ARC
Heck, AJR
Kenny, JA
Kettenes-van den Bosch, JJ
Wills, M
TETRAHEDRON-ASYMMETRY, 1999, 10 (17) : 3267 - 3271
[39] Studies on enzymatic synthesis of chiral non-racemic 3-arylglutaric acid monoesters
Fryszkowska, Anna
Komar, Marta
Koszelewski, Dominik
Ostaszewski, Ryszard
TETRAHEDRON-ASYMMETRY, 2006, 17 (06) : 961 - 966
[40] CHIRAL (NON-RACEMIC) 4-SUBSTITUTED QUINOLIZIDINES - SYNTHESIS AND CONFORMATIONAL-ANALYSIS
MCINTOSH, JM
MATASSA, LC
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 146 - ORGN

← 1 2 3 4 5 →