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

[1] On the Absolute Configuration of Chiral 1,4-Dihydropyridazines Synthesized by Organocatalysed Reactions
Lin, Na
Forzato, Cristina
Berti, Federico
Felluga, Fulvia
Nitti, Patrizia
Pitacco, Giuliana
Coriani, Sonia
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (23): : 11670 - 11679
[2] Novel and Convenient Synthesis of 1,4-Dihydropyridazines and Pyridazines from Aminocarbonylazoalkenes
Attanasi, O. A.
Filippone, P.
Fiorucci, C.
Mantellini, F.
Synlett, (12):
[3] Novel and convenient synthesis of 1,4-dihydropyridazines and pyridazines from aminocarbonylazoalkenes
Attanasi, OA
Filippone, P
Fiorucci, C
Mantellini, F
SYNLETT, 1997, (12) : 1361 - 1362
[4] SYNTHESIS AND THERMOLYSIS OF A CHIRAL, NON-RACEMIC IMINOAZIRIDINE
QUAST, H
ALDENKORTT, S
HELLER, E
SCHAFER, P
SCHMITT, E
CHEMISCHE BERICHTE, 1994, 127 (09) : 1699 - 1706
[5] A new synthetic approach to fused 1,4-dihydropyridazines
Yamasaki, T
Oda, M
Okamoto, Y
Okawara, T
Furukawa, M
HETEROCYCLES, 1996, 43 (09) : 1863 - 1871
[6] Addition of a chiral non-racemic silyloxypyrrole to anactivated 1,4-benzoquinone
Halim, R
Brimble, MA
Woodgate, PD
ARKIVOC, 2002, : 61 - 70
[7] Synthesis of 1-Carboxamide-1,4-dihydropyridazines via Recyclization of Hydroxypyrrolines with Semicarbazides
Shabalin, Dmitrii A.
Ivanova, Evgeniya E.
Kuzmin, Anton V.
Dvorko, Marina Yu.
Schmidt, Elena Yu.
Trofimov, Boris A.
SYNTHESIS-STUTTGART, 2018, 50 (24): : 4982 - 4988
[8] Synthesis of chiral non-racemic substituted vinyl aziridines
Chigboh, Kordi
Morton, Daniel
Nadin, Alan
Stockman, Robert A.
TETRAHEDRON LETTERS, 2008, 49 (32) : 4768 - 4770
[9] ω-Transaminases for the synthesis of non-racemic α-chiral primary amines
Koszelewski, Dominik
Tauber, Katharina
Faber, Kurt
Kroutil, Wolfgang
TRENDS IN BIOTECHNOLOGY, 2010, 28 (06) : 324 - 332
[10] Straightforward synthesis of chiral non-racemic α-boryl isocyanides
Fini, Francesco
Zanni, Alessandro
Introvigne, Maria Luisa
Stucchi, Mattia
Caselli, Emilia
Prati, Fabio
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (30) : 6687 - 6691

← 1 2 3 4 5 →