TADDOL-Based Titanium Catalysts and Their Adducts: Understanding Asymmetric Catalysis of Diels-Alder Reactions

1995 ◽  
Vol 60 (6) ◽  
pp. 1777-1787 ◽  
Author(s):  
Cornelius Haase ◽  
Christopher R. Sarko ◽  
Marcello DiMare
Keyword(s):  
Asymmetric Catalysis ◽  
Diels Alder ◽  
Titanium Catalysts

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

scholarly journals Titelbild: Diversified Cycloisomerization/Diels–Alder Reactions of 1,6‐Enynes through Bimetallic Relay Asymmetric Catalysis (Angew. Chem. 16/2019)

2019 ◽  
Vol 131 (16) ◽  
pp. 5191-5191
Author(s):  
Haifeng Zheng ◽  
Yan Wang ◽  
Chaoran Xu ◽  
Qian Xiong ◽  
Lili Lin ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Diels Alder

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.

Diversified Cycloisomerization/Diels–Alder Reactions of 1,6‐Enynes through Bimetallic Relay Asymmetric Catalysis

2019 ◽  
Vol 58 (16) ◽  
pp. 5327-5331 ◽  
Author(s):  
Haifeng Zheng ◽  
Yan Wang ◽  
Chaoran Xu ◽  
Qian Xiong ◽  
Lili Lin ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Diels Alder

Asymmetric Catalysis of (Hetero) Diels-Alder Cycloadditions by a Modified Binaphthol-derived Titanium Complex

Synlett ◽  
1995 ◽  
Vol 1995 (09) ◽  
pp. 967-968 ◽  
Author(s):  
Yukihiro Motoyama ◽  
Masahiro Terada ◽  
Koichi Mikami
Keyword(s):  
Asymmetric Catalysis ◽  
Diels Alder ◽  
Titanium Complex
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