1256152-03-0Relevant 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
supporting information, p. 3131 - 3137 (2015/05/20)
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.
Redox-neutral atom-economic rhodium-catalyzed coupling of terminal alkynes with carboxylic acids toward branched allylic esters
Lumbroso, Alexandre,Koschker, Philipp,Vautravers, Nicolas R.,Breit, Bernhard
supporting information; experimental part, p. 2386 - 2389 (2011/05/04)
A new method for the preparation of a wide range of branched allylic esters from terminal alkynes that proceeds via a redox-neutral propargylic CH activation employing a rhodium(I)/DPEphos catalyst is reported.
Rhodium-catalyzed selective anti -markovnikov addition of carboxylic acids to alkynes
Lumbroso, Alexandre,Vautravers, Nicolas R.,Breit, Bernhard
supporting information; experimental part, p. 5498 - 5501 (2011/02/24)
The selective intermolecular anti-Markovnikov addition of carboxylic acids to terminal alkynes yielding valuable Z-enol esters has been achieved for the first time under rhodium-catalyzed conditions. The catalyst system is applicable to a broad substrate
