Challenge toward Structural Complexity Using Asymmetric Catalysis:  Target-Oriented Development of Catalytic Enantioselective Diels−Alder Reaction

2004 ◽  
Vol 6 (23) ◽  
pp. 4387-4390 ◽  
Author(s):  
Hiroyuki Usuda ◽  
Akiyoshi Kuramochi ◽  
Motomu Kanai ◽  
Masakatsu Shibasaki
Keyword(s):  
Asymmetric Catalysis ◽  
Structural Complexity ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Asymmetric Catalysis of the Transannular Diels-Alder Reaction

Science ◽  
2007 ◽  
Vol 317 (5845) ◽  
pp. 1736-1740 ◽  
Author(s):  
E. P. Balskus ◽  
E. N. Jacobsen
Keyword(s):  
Asymmetric Catalysis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

An examination of VANOL, VAPOL, and VAPOL derivatives as ligands for asymmetric catalytic Diels–Alder reactions

2006 ◽  
Vol 84 (10) ◽  
pp. 1487-1503 ◽  
Author(s):  
Douglas P Heller ◽  
Daniel R Goldberg ◽  
Hongqiao Wu ◽  
William D Wulff
Keyword(s):  
Asymmetric Catalysis ◽  
Methyl Acrylate ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Catalytic ◽  
Diels Alder Reaction ◽  
Positive Cooperativity ◽  
Derivatives Of ◽  
Methyl Phenyl

Several derivatives of the vaulted biaryl ligand VAPOL were prepared and evaluated as chiral ligands for aluminum Lewis acids in the catalytic asymmetric Diels–Alder reactions of methyl acrylate and methacrolein with cyclopentadiene. The substituents on VAPOL were introduced into the 6- and 6′-positions in an effort to further extend the chiral pocket of the major groove, which contains the phenol functions at the 4- and 4′-positions. The set of four new ligands that have been prepared have the following groups introduced into the 6- and 6′-positions of VAPOL: bromide, methyl, phenyl and 3,5-di-t-butylphenyl. All of these ligands give lower asymmetric inductions than the unsubstituted VAPOL for the Diels–Alder reactions of both methyl acrylate and methacrolein. The positive cooperativity of added carbonyl compounds on the autoinduction in the Diels–Alder reaction of methyl acrylate and cyclopentadiene were also investigated with the VANOL and VAPOL ligands as well as the 6,6′-dibromo and 6,6′-diphenyl derivatives of VAPOL. Only the reaction with VAPOL showed any significant positive cooperativity. The reaction with VANOL was sluggish at –78 °C, but at higher temperatures, the reaction did exhibit positive cooperativity that was similar to that of VAPOL. Finally, no positive cooperativity was observed with the VAPOL ligand for the reaction of methacrolein and cyclopentadiene.Key words: Diels–Alder, asymmetric catalysis, vaulted biaryl ligands, VANOL, VAPOL.

ChemInform Abstract: Asymmetric Catalysis of Diels-Alder Reaction

ChemInform ◽  
2010 ◽  
Vol 41 (31) ◽  
pp. no-no
Author(s):  
Haifeng Du ◽  
Kuiling Ding
Keyword(s):  
Asymmetric Catalysis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Heterogeneous asymmetric catalysis

2004 ◽  
Vol 76 (3) ◽  
pp. 679-688 ◽  
Author(s):  
Marc Lemaire
Keyword(s):  
Asymmetric Catalysis ◽  
Supported Catalysts ◽  
Asymmetric Reduction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Catalyst Precursor ◽  
Iridium Complexes ◽  
Diels Alder Reaction ◽  
Polystyrene Matrix ◽  
Enantioselective Catalysts

Examples of enantioselective catalysts, including homogeneous supported catalysts and biphasic liquid/liquid, are described and compared. In the case of asymmetric hydride transfer, polythiourea was proven to be more efficient for ruthenium-catalyzed reduction of arylketones, although the iridium complexes gave rise to higher ee when using amino sulfonamide bound to a polystyrene matrix. In the case of asymmetric reduction, the modification of the binap allows the formation of a polymer that could be used as a catalyst precursor and exhibits enantioselectivities as high as observed in solution, but easier to separate and recycle. Bisoxazoline bound to silica particules could also be used in copper-catalyzed asymmetric Diels-Alder reaction and cyclopropanation with selectivities similar to that obtained in solution.

4-Naphthyl-substituted bis(oxazoline): A new, easily recoverable and efficient chiral ligand in asymmetric catalysis of the Diels-Alder reaction

Tetrahedron ◽  
1998 ◽  
Vol 54 (51) ◽  
pp. 15721-15730 ◽  
Author(s):  
Stefano Crosignani ◽  
Giovanni Desimoni ◽  
Giuseppe Faita ◽  
PierPaolo Righetti
Keyword(s):  
Asymmetric Catalysis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Ligand ◽  
Diels Alder Reaction

Asymmetric Catalysis of the Diels−Alder Reaction Using Dicationic Zirconocene Complexes

2000 ◽  
Vol 19 (6) ◽  
pp. 947-949 ◽  
Author(s):  
Georgiy V. Bondar ◽  
Raluca Aldea ◽  
Christopher J. Levy ◽  
James B. Jaquith ◽  
Scott Collins
Keyword(s):  
Asymmetric Catalysis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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