72853-48-6Relevant academic research and scientific papers
The conjugate addition-aldol tandem reaction of α,β-unsaturated esters catalyzed by lithium benzenethiolate
Ono, Masashi,Nishimura, Katsumi,Nagaoka, Yasuo,Tomioka, Kiyoshi
, p. 1509 - 1512 (1999)
Reactions of α,β-unsaturated esters with aldehydes were catalyzed by 0.2 equiv of lithium benzenethiolate in the presence of phenyl trimethylsilyl sulfide to afford the conjugate addition-aldol tandem reaction products in the anti stereoselectivity and go
Z/E selective synthesis of β,β-disubstituted and (Z)-β- monosubstituted Baylis-Hillman adducts via anionic additions of vinylcuprates to aldehydes
Wei, Han-Xun,Willis, Steven,Li, Guigen
, p. 2959 - 2966 (1999)
A new method has been developed for the synthesis of achiral β,β- disubstituted and (Z)-β-monosubstituted Baylis-Hillman adducts with excellent Z/E stereospecificity in some cases. The process involves the conjugate additions of R2CuLi or RMgBr-CuBr-DMS to α,β-acetylenic esters and followed by additions of anionic α-(alkoxycarbonyl)vinyl]copper intermediates to aldehydes. The individual Z- and E- isomers of the resulting β-branched α-(hydroxylalkyl)acrylates can be separated by column chromatography in modest to excellent yield.
An efficient approach to (E)-β-methyl Baylis-Hillman adducts via indium-mediated allylation of aldehydes in aqueous media
Cha, Joo Hwan,Pae, Ae Nim,Choi, Kyung Il Il,Cho, Yong Seo,Koh, Hun Yeong,Lee, Eun
, p. 2079 - 2081 (2007/10/03)
A new method has been developed for the synthesis of (E)-β-methyl Baylis-Hillman adducts with high E-Z (>93%) selectivity in modest to good yields. The process consists of two steps: an indium-mediated allylation reaction and a simple base-catalyzed isomerization step. Various aldehydes were allylated with allyl bromides using indium under very mild conditions in aqueous media. The allylation reactions of aromatic and aliphatic aldehydes were largely accelerated by the presence of HCl.
A General Synthesis of 5,6-Dihydro-α-pyrones
Dugger, R.W.,Heathcock, Clayton H.
, p. 1181 - 1185 (2007/10/02)
Crotonate esters substituted at C-3 by alkyl, alkoxy, or dialkylamino groups are deprotonated and the resulting dienolates added to aldehydes and ketones.Kinetic reaction is at C-2 of the ester, leading to the isolation of 2-alkyl-3-hydroxy esters such as 3 and 4 if the reaction mixture is quenched at -70 deg C.However, retroaldolization occurs readily.If the initial reaction mixtures are allowed to warm to 15 deg C before workup, the isolated products are 5,6-dihydro-α-pyrones (such as 5), accompanied in some cases by the (E)-4-substituted crotonate (such as 6).The method has been applied to the synthesis of a series of retinoid lactones (5f,18,21a-c) which are of interest as potential antineoplastic agents.
