63859-84-7Relevant academic research and scientific papers
Mechanistic switch leading to highly efficient chirality transfer in Pd(0)-catalyzed coupling-cyclization of aryl iodides with 1:1 acid-base salts of 2,3-allenoic acids and L-(-)-cinchonidine or D-(+)-/L-(-)-α-methylbenzylamine. Enantioselective synthesis
Ma, Shengming,Shi, Zhangjie
, p. 540 - 541 (2002)
An efficient methodology provides an easy access to highly optically active polysubstituted butenolides starting from aryl halides and 1:1:salts of optically active 2,3-allenoic acid-base via an oxidative addition-coordinative cyclization-reductive elimin
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
