87351-46-0Relevant academic research and scientific papers
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.
Chemistry of Substituted (α-Carbethoxyvinyl)cuprates. 2. Stereospecific Olefin Synthesis
Marino, Joseph P.,Linderman, Russell J.
, p. 4621 - 4628 (2007/10/02)
The reactivity of substituted (α-carbethoxyvinyl)cuprate reagents with various electrophiles has been studied systematically.The reaction of this type of cuprate reagent with ketones and epoxides leads to high yields of isomerically pure olefinic esters, while its condensation reaction with aldehydes produced mixtures of isomers.The stereochemistry of the condensation reaction with carbonyl compounds is explained by a steric control mechanism involving an allenoate intermediate.
