Bis (trimethylsilyl) Sulfate Catalysis in γ-Lactonization of Cyclopropanecarboxylates Activated by Carbonyl Substituents on α-Carbon

Y Morizawa, T Hiyama, K Oshima…

Index: Morizawa, Yoshitomi; Hiyama, Tamejiro; Oshima, Koichiro; Nozaki, Hitosi Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 4 p. 1123 - 1127

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Citation Number: 18

Abstract

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 ...

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