37112-25-7Relevant articles and documents
Synthesis of chiral α-diarylacetic esters by stereospecific 1,2-aryl migration promoted by in situ generated acetals from benzoins
Kothapalli, Raveendra Babu,Niddana, Ramana,Balamurugan, Rengarajan
supporting information, p. 1278 - 1281 (2014/04/03)
A simple protocol for the synthesis of α-diarylacetic esters from benzoins is described. In situ generated acetal assists rapid 1,2-aryl migration in a stereospecific manner, paving the way to make enantioenriched α-diarylacetic esters from easily accessi
Chemoselective N-heterocyclic carbene-catalyzed cross-benzoin reactions: Importance of the fused ring in triazolium salts
Langdon, Steven M.,Wilde, Myron M.D.,Thai, Karen,Gravel, Michel
supporting information, p. 7539 - 7542 (2014/06/10)
Morpholinone- and piperidinone-derived triazolium salts are shown to catalyze highly chemoselective cross-benzoin reactions between aliphatic and aromatic aldehydes. The reaction scope includes ortho-, meta-, and para-substituted benzaldehyde derivatives with a range of electron-donating and -withdrawing groups as well as branched and unbranched aliphatic aldehydes. Catalytic loadings as low as 5 mol % give excellent yields in these reactions (up to 99%).
Highly chemoselective direct crossed aliphatic-aromatic acyloin condensations with triazolium-derived carbene catalysts
O'Toole, Sarah E.,Rose, Christopher A.,Gundala, Sivaji,Zeitler, Kirsten,Connon, Stephen J.
supporting information; experimental part, p. 347 - 357 (2011/04/17)
It has been shown for the first time that triazolium precatalysts promote (in the presence of base) highly chemoselective crossed acyloin condensation reactions between aliphatic and ortho-substituted aromatic aldehydes. An o-bromine atom can serve as a temporary directing group to ensure high chemoselectivity (regardless of the nature of the other substituents on the aromatic ring) which then can be conveniently removed. The process is of broad scope and is operationally simple as it does not require the preactivation of any of the coupling partners to ensure selectivtiy. Preliminary data indicate that highly enantioselective variants of the reaction are feasible using chiral precatalysts.