945486-19-1Relevant academic research and scientific papers
Synthesis of γ-acetoxy β-keto esters through regioselective hydration of γ-acetoxy-α,β-alkynoates
Pradhan, Tapas R.,Mendhekar, Kishor L.,Mohapatra, Debendra K.
, p. 5517 - 5531 (2015/06/16)
The Au(I)-catalyzed regioselective hydration of γ-acetoxy-α,β-acetylinic ester by the assistance of a neighboring carbonyl group has been developed. Varieties of simple primary, secondary, and tertiary γ-acetoxy-α,β-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding β-keto esters. The reaction tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. 18O labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.
Metal-free access to fully substituted skipped diynes. An efficient chemodifferentiating A2BB′ 4CR manifold
Tejedor, David,Lopez-Tosco, Sara,Gonzalez-Platas, Javier,Garcia-Tellado, Fernando
, p. 5454 - 5456 (2008/02/08)
(Chemical Equation Presented) A metal-free chemodifferentiating A 2BB′ 4CR manifold for the modular synthesis of tertiary skipped diynes is described. The manifold performs a triethylamine triggered reaction of alkyl propiolates and acid chlori
