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
Full Text: HTML
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 ...
Related Articles:
[Szostak, Michal; Spain, Malcolm; Choquette, Kimberly A.; Flowers, Robert A.; Procter, David J. Journal of the American Chemical Society, 2013 , vol. 135, # 42 p. 15702 - 15705]
The formation of enolates from lactonic esters
[Michael; Weiner Journal of the American Chemical Society, 1936 , vol. 58, p. 999,1002]
[van Tamelen; Bach Journal of the American Chemical Society, 1958 , vol. 80, p. 3079,3083]
The formation of enolates from lactonic esters
[Michael; Weiner Journal of the American Chemical Society, 1936 , vol. 58, p. 999,1002]
[Boehrer, Gerald; Knorr, Rudolf; Boehrer, Petra Chemische Berichte, 1990 , vol. 123, # 11 p. 2161 - 2166]