895170-18-0Relevant academic research and scientific papers
Palladium-catalyzed carbonylative cyclization of Baylis-Hillman adducts. An efficient approach for the stereoselective synthesis of 3-alkenyl phthalides
Coelho, Fernando,Veronese, Demetrius,Pavam, Cesar H.,de Paula, Vanderlei I.,Buffon, Regina
, p. 4563 - 4572 (2006)
A palladium-mediated carbonylative cyclization reaction of Baylis-Hillman adducts is disclosed. This simple, efficient and straightforward sequence leads to the formation of an array of 3-alkenylphthalides with different substitution patterns on the aromatic ring, with good chemical yields and selectivities.
Employing Small Polyfunctionalized Molecules for a Diastereoselective Synthesis of Highly Substituted Indolines
de Souza Fernandes, Fábio,Cormanich, Rodrigo A.,Zeoly, Lucas A.,Formiga, André Luiz B.,Coelho, Fernando
, p. 3211 - 3223 (2018/07/06)
An efficient approach has been developed for the diastereoselective synthesis of 1,2,3-trisubstituted indolines. The reaction sequence includes the highly diastereoselective reductive amination of 2-oxo-1,3-propanediols, which are prepared by postfunctionalization of Morita–Baylis–Hillman (MBH) adducts, to give substituted 2-amino-1,3-propanediols with an anti relative configuration. A subsequent intramolecular palladium-catalyzed Buchwald coupling reaction provided the 1,2,3-trisubstituted indolines in 47–82 % yield. The preference for the anti diastereomer was investigated by Gibbs free energy diagrams and applying theoretical calculations at the M06–2X/6-31+G** level.
