119590-52-2Relevant academic research and scientific papers
An expedient synthesis of 3-arylmethylbutenolides from α-methylene- γ-butyrolactones: A useful synthetic application of palladium-catalyzed chelation-controlled oxidative arylation protocol
Kim, Se Hee,Kim, Ko Hoon,Lee, Hyun Ju,Kim, Jae Nyoung
, p. 329 - 334 (2013/03/13)
A palladium-catalyzed chelation-controlled oxidative arylation of α-methylene-γ-butyrolactones with arenes provided 3-arylmethylbutenolides as major products along with a low yield of α-arylidene-γ-butyrolactones. The selectivity might be due to a chelation between the palladium center and a directing group at the γ-position of α-methylene-γ-butyrolactones.
Heteroatom-guided torquoselective olefination of α-oxy and α-amino ketones via ynolates
Shindo, Mitsuru,Yoshikawa, Takashi,Itou, Yasuaki,Mori, Seiji,Nishii, Takeshi,Shishido, Kozo
, p. 524 - 536 (2008/09/20)
Ynolates were found to react with α-alkoxy-, α-siloxy-, and α -aryloxyketones at room temperature to afford tetrasubstituted olefins with high Z selectivity. Since the geometrical selectivity was determined in the ring opening of the β-lactone enolate intermediates, the torquoselectivity was controlled by the ethereal oxygen atoms. From experimental and theoretical studies, the high Z selectivity is in duced by orbital and steric interactions rather than by chelation. In a similar manner, α-dialkylamino ketones provided olefins with excellent Z selectivity. These products can be easily converted into multisubstituted butenolides and γ-butyrolactams in good yield.
ANODIC SYNTHESIS OF BUTENOLIDES FROM β-ETHYLENIC ESTERS DOUBLE CYCLIZATION IN THE PRESENCE OF OLEFINS
Delaunay, J.,Orliac-Le Moing, A.,Simonet, J.
, p. 7089 - 7094 (2007/10/02)
Anodic oxidation of β-ethylenic esters yields butenolides 2.In the presence of 1-phenyl-1-propene or α,β-disubstituted indenones a double cyclization takes place to yield more complex butenolides
