57221-98-4Relevant academic research and scientific papers
Enantioselective redox-neutral Rh-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters
Koschker, Philipp,K?hny, Matthias,Breit, Bernhard
, p. 3131 - 3137 (2015)
We report on the first enantioselective variant of the atom-economic and redox-neutral coupling of carboxylic acids with terminal alkynes under rhodium catalysis utilizing the chiral, bidentate (R,R)-Cp-DIOP ligand. This represents the first example of this convenient asymmetric access to valuable branched allylic esters. The utility of this methodology is demonstrated by both a reaction performed on large scale and a short three-step synthesis of two naturally occurring γ-butyrolactones. A stereochemical model explaining the observed absolute configuration of the products based on DFT calculations is given.
