Synthesis of nucleosides and related compounds. XIV. Diels-Alder reaction of di-l-menthyl acetoxymethylenemalonate with cyclopentadiene: Effects of high-pressure and catalysts upon asymmetric induction.

1990 ◽  
Vol 38 (1) ◽  
pp. 69-72 ◽  
Author(s):  
Nobuya KATAGRI ◽  
Nobuhisa WATANABE ◽  
Chikara KANEKO
Keyword(s):  
High Pressure ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Induction ◽  
Diels Alder Reaction ◽  
Related Compounds

scholarly journals Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

2015 ◽  
Vol 11 ◽  
pp. 576-582 ◽  
Author(s):  
Grzegorz Mlostoń ◽  
Paulina Grzelak ◽  
Maciej Mikina ◽  
Anthony Linden ◽  
Heinz Heimgartner
Keyword(s):  
High Pressure ◽  
Room Temperature ◽  
Thermal Conditions ◽  
Alder Reaction ◽  
Diels Alder ◽  
Hydrogen Shift ◽  
Diels Alder Reaction ◽  
Shift Sequence

Selected hetaryl and aryl thioketones react with acetylenecarboxylates under thermal conditions in the presence of LiClO4 or, alternatively, under high-pressure conditions (5 kbar) at room temperature yielding thiopyran derivatives. The hetero-Diels–Alder reaction occurs in a chemo- and regioselective manner. The initially formed [4 + 2] cycloadducts rearrange via a 1,3-hydrogen shift sequence to give the final products. The latter were smoothly oxidized by treatment with mCPBA to the corresponding sulfones.

Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction

1980 ◽  
Vol 102 (22) ◽  
pp. 6893-6894 ◽  
Author(s):  
William G. Dauben ◽  
Carl R. Kessel ◽  
Kazuo H. Takemura
Keyword(s):  
High Pressure ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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