Asymmetric Induction in the Diels-Alder Reaction Catalyzed by Chiral Metallocene Triflate Complexes: Dramatic Effect of Solvent Polarity

1995 ◽  
Vol 14 (3) ◽  
pp. 1079-1081 ◽  
Author(s):  
James B. Jaquith ◽  
Jinying Guan ◽  
Shaotian Wang ◽  
Scott Collins
Keyword(s):  
Solvent Polarity ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Induction ◽  
Dramatic Effect ◽  
Effect Of Solvent ◽  
Diels Alder Reaction

Catalytic asymmetric induction in the homo Diels-Alder reaction

1990 ◽  
Vol 112 (14) ◽  
pp. 5627-5628 ◽  
Author(s):  
Mark Lautens ◽  
Julia Craig Lautens ◽  
A. Catherine Smith
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Induction ◽  
Diels Alder Reaction ◽  
Catalytic Asymmetric

Diastereoselectivity and asymmetric induction in the Diels–Alder reaction of o-quinodimethanes

1986 ◽  
Vol 64 (4) ◽  
pp. 720-725 ◽  
Author(s):  
James L. Charlton
Keyword(s):  
Maleic Anhydride ◽  
Methyl Acrylate ◽  
Dimethyl Fumarate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Induction ◽  
Diels Alder Reaction ◽  
The Absolute ◽  
Alkoxy Groups

The extent of asymmetric induction in the bimolecular Diels–Alder reactions of chiral o-quinodimethanes with dimethyl fumarate, methyl acrylate, and maleic anhydride has been studied. o-Quinodimethanes with chiral α-alkoxy groups were prepared from 1-alkoxy-1,3-dihydrobenzo[c]thiophene-2,2-dioxides 4a–f or 1-alkoxy-3-phenyl-1,3-dihydrobenzo[c]thiophene-2,2-dioxides 4g–h by thermolysis. These alkoxybenzosulfones were prepared from the corresponding hydroxybenzosulfones 8 and 1-phenylethanol, 2-phenyl-1-propanol, 4-phenyl-2-butanol, 1-phenyl-2-propanol, 3,3-dimethyl-2-butanol, or 1-cyclo-hexylethanol. The 1-phenylethoxy substituent yielded the largest asymmetric induction. The absolute configurations of the major cycloadducts of methyl acrylate with the o-quinodimethanes generated from 1-(R- 1-phenylethoxy)- and 1-(S-1-phenylethoxy)-1,3-dihydrobenzo[c]thiophene-2,2-dioxides 4i and 4j have been determined to be 1S,2S-1-(R-1-phenylethoxy)- and 1R,2R-1-(S-1-phenylethoxy)-2-carbomethoxy-1,2,3,4-tetrahydronaphthalene 11i and 11j, respectively. The proposition that a chiral alkoxy substituent can block one face of the o-quinodimethane towards addition of a dienophile is discussed.

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