124578-13-8Relevant articles and documents
Oxo-Diels-Alder reaction of danishefskys diene with aldehydes, catalyzed by chiral tridentate chromium(III)-Schiff base complexes
Miesowicz, Sawomir,Chaladaj, Wojciech,Jurczak, Janusz
, p. 1421 - 1425 (2010)
The enantioselective hetero-Diels-Alder reaction of Danishefskys diene with simple aromatic and aliphatic aldehydes is catalyzed by chiral tridentate Schiff base-chromium(III) complexes. In many cases, 2,3-dihydropyran-4-ones are obtained in good yields (
Asymmetric hetero Diels-Alder reaction using chiral cationic metallosalen complexes as catalysts
Aikawa, Kohsuke,Irie, Ryo,Katsuki, Tsutomu
, p. 845 - 851 (2001)
Chiral cationic (R,S)- or (R,R)-(salen)-manganese(III) and -chromium(III) complexes served as the catalysts for asymmetric hetero Diels-Alder reaction of Danishefsky's diene with aldehydes, achieving high enantioselectivity (up to 97% ee at 0°C). The reac
Photo-controlled Lewis acidity: Chiral (ON)Ru-salen catalyzed hetero Diels-Alder reaction and kinetic resolution of racemic epoxides
Mihara, Jun,Hamada, Tetsuya,Takeda, Tsuyoshi,Irie, Ryo,Katsuki, Tsutomu
, p. 1160 - 1162 (1999)
(ON+)(Salen)ruthenium(II) complex 1 serves as a chiral Lewis acid catalyst for asymmetric hetero Diels-Alder reaction and for kinetic resolution of racemic epoxides when the reactions were carried out under sunlight coming through windows or incandescent light.
Systematically probing the effect of catalyst acidity in a hydrogen-bond-catalyzed enantioselective reaction
Jensen, Katrina H.,Sigman, Matthew S.
, p. 4748 - 4750 (2007)
(Chemical Equation Presented) Defining the relationship: The effect of catalyst acidity has been systematically probed by using a modular oxazoline catalyst in a hetero-Diels-Alder reaction catalyzed by hydrogen bonding. Linear free energy relationships w
Assembled Dendritic Titanium Catalysts for Enantioselective Hetero-Diels-Alder Reaction of Aldehydes with Danishefsky's Diene
Ji, Baoming,Yuan, Yu,Ding, Kuiling,Meng, Jiben
, p. 5989 - 5996 (2003)
A new type of dendritic 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN)-derived Schiff-base ligands have been synthesized and applied to the titanium-catalyzed hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes. These reactions afforded the corresponding 2-substituted 2,3-dihydro-4H-pyran-4-ones in quantitative yields and with excellent enantioselectivities (up to 97.2% ee). The disposition of the dendritic wedges and the dendron size in the ligands were found to have significant impact on the enantioselectivity of the reaction. The recovered dendritic catalyst could be reused without further addition of the Ti source or a carboxylic acid additive for at least three cycles, retaining similar activity and enantioselectivity. The high stability of this type of assembled dendritic titanium catalyst may be attributed to the stabilization effect of large-sized dendron units in the catalyst molecule. The other important phenomenon observed with this catalyst system is that a higher degree of asymmetric amplification has been achieved by attachment of the dendron unit to the chiral ligand, which represents a new advantage of dendrimer catalysts for asymmetric reactions using chiral ligands of lower optical purity.
Enantioselective catalysis of hetero Diels-Alder reaction and diethylzinc addition using a single catalyst
Du, Haifeng,Ding, Kuiling
, p. 1091 - 1093 (2003)
(Matrix presented) Integration of two asymmetric reactions in one pot with the promotion of a single catalyst has been achieved in high efficiency and excellent stereoselectivity for hetero Diels-Alder reaction of Danishefsky's diene and diethylzinc addit
BINOlate-magnesium catalysts for enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes
Du, Haifeng,Zhang, Xue,Wang, Zheng,Bao, Hongli,You, Tianpa,Ding, Kuiling
, p. 2248 - 2254 (2008)
An efficient catalytic enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes using the magnesium binaphthoxide system has been developed, affording a variety of 2-substituted 2,3-dihydro-4H-pyran-4-ones in high yields and with
Polyglycerol-supported chromium-salen as a high-loading dendritic catalyst for stereoselective Diels-Alder reactions
Hajji, Chakib,Roller, Sebastian,Beigi, Maryam,Liese, Andreas,Haag, Rainer
, p. 1760 - 1771 (2006)
In this paper we demonstrate the application of hyperbranched polyglycerol (PG) 3 as a polymeric support for asymmetric catalysis. A new polyglycerol-supported unsymmetrical salen ligand 4 is described, which was successfully purified by gel permeation chromatography (GPC) or by ultrafiltration. After the insertion of the metal, e.g., chromium, the corresponding polymeric chromium complex was used as catalyst for asymmetric Diels-Alder reactions between Danishefsky's diene and benzaldehyde. The catalytic activities (up to 98% conversion) and enantioselectivities (up to 78% ee) were comparable to the original catalyst reported by Jacobsen. The soluble polyglycerol-supported catalysts were recovered by dialysis after the catalytic reactions and were recycled two times to afford identical reactivities as in the first run, with slightly reduced enantioselectivities. Moreover, this polymeric support catalyst showed a high retention (99.02%) in a continuously operated membrane reactor.
Highly asymmetric hetero-Diels-Alder reaction using helical silica-supported Mn(III)-salen catalysts
Li, Le,Li, Yu,Pang, Di,Liu, Fei,Zheng, Aqun,Zhang, Guangbin,Sun, Yang
, p. 8096 - 8103 (2015)
Helical silica were prepared and functionalized by Mn(III)-salen complexes in order to catalyze asymmetric hetero-Diels-Alder reactions. Characterizations revealed doping of sodium lactate facilitated porosity, hydrolysis resistance and chiral configurati
DIANANE-CrIII-salen complexes as highly enantioselective catalysts for hetero-Diels-Alder reactions of aldehydes with dienes
Berkessel, Albrecht,Vogl, Nadine
, p. 5029 - 5035 (2006)
A new type of chromium-salen complex bearing DIANANE (endo,endo-2,5- diaminonorbornane) as chiral backbone has been synthesized and applied to the hetero-Diels-Alder reaction of Danishefsky's diene with various aldehydes. The reactions afford the correspo
