79011-89-5Relevant academic research and scientific papers
Bis(trimethylsilyl) Sulfate Catalysis in γ-Lactonization of Cyclopropanecarboxylates Activated by Carbonyl Substituents on α-Carbon
Morizawa, Yoshitomi,Hiyama, Tamejiro,Oshima, Koichiro,Nozaki, Hitosi
, p. 1123 - 1127 (2007/10/02)
The title reaction of 1-carbonyl substituted cyclopropanecarboxylates proceeds under C(1)-C(2) bond cleavage to produce γ-lactones.Stereochemically, the reaction takes two pathways: (1) substrates with a cationstabilizing group like vinyl on C(2) give thermodynamically favored γ-lactones having the thermodynamically more stable arrangement of substituents irrespective of the configuration of the cyclopropane substrates, (2) substrates without such a cation-stabilizing group afford γ-lactones under ca. 70percent inversion at C(2) reaction center.
BIS(TRIMETHYLSILYL) SULPHATE CATALYZED γ-LACTONIZATION OF CYCLOPROPANECARBOXYLATES HAVING A CARBONYL SUBSTITUENT AT CYCLOPROPANE α-CARBON
Morizawa, Yoshitomi,Hiyama, Tamejiro,Nozaki, Hitosi
, p. 2297 - 2300 (2007/10/02)
The oxa analogue of vinylcyclopropane rearrangement in the title system is carried out under mild conditions with the aid of the silicon Lewis acid catalyst.
