746677-92-9Relevant academic research and scientific papers
Synthesis of (-)-α-Kainic Acid via TMSCl-Promoted Pd-Catalyzed Zinc-ene Cyclization of an Allyl Acetate
Wei, Guoqing,Chalker, Justin M.,Cohen, Theodore
experimental part, p. 7912 - 7917 (2011/12/01)
A highly practical synthesis of enantiopure (-)-α-kainic acid is accomplished in 37% overall yield, using 13 linear steps and a minimum of chromatographic separations via an unprecedentedTMSClpromoted palladium-catalyzed zinc-ene cyclization of an allyl acetate. (Figure presented)
First generation cysteine- and methionine-derived oxazolidine and thiazolidine ligands for palladium-catalyzed asymmetric allylations
Schneider, Paulo H.,Schrekker, Henri S.,Silveira, Claudio C.,Wessjohann, Ludger A.,Braga, Antonio L.
, p. 2715 - 2722 (2007/10/03)
A new series of enantiopure oxazolidine-thioether and thiazolidine-alcohol ligands have been synthesized from L-cysteine, S-methyl-L-cysteine, and L-methionine in a straightforward manner that allows numerous structural variations to be formed. These types of ligands have not previously been used in asymmetric palladium-catalyzed allylations and their efficacy was explored in the reaction of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate. The reaction proceeds in excellent yield and with good enantioselectivity. The palladium catalyst derived from N-benzyl-2,2-dimethyl-4-(2-thiapropyl) oxazolidine (12) provides the allylation product in a quantitative yield and with an enantiomeric excess of 94%. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
