Gold(I)- and Yb(OTf)3-Cocatalyzed rearrangements of epoxy alkynes: Transfer of a carbonyl group in a five-membered carbocycle
We report here the intramolecular reactions between α,β-epoxy ketones and alkynes cocatalyzed by gold(I) and Yb(OTf)3. This new catalytic system based on a combination of gold(I) and Yb (OTf)3 allows facile transformation of epoxy alkynes to give novel indene derivatives in moderate to good yields under mild conditions. Moreover, we describe here the first observation of a transfer of a carbonyl group in a five-membered carbocycle during gold-catalyzed reactions. This proposed mechanism is corroborated by isotope-labeling experiments (D and 13C). Furthermore, the probable role of each catalyst in this interesting domino reaction has been examined by 31P NMR experiments. The utilization of gold catalysts combined with rareearth metal salts offers a new concept for the design of catalyst combinations for domino or cascade reactions.
Dai, Lun-Zhi,Shi, Min
supporting information; experimental part
p. 2496 - 2502
(2010/06/20)
An investigation of the conformation of 4-chloroethylbenzene as a solut e in a nematic liquid crystalline solvent
The conformation of the ethyl group relative to the phenyl ring plane in 4-chloroethylbenzene has been investigated by recording and analysing the proton NMR spectrum of a sample dissolved in a nematic liquid crystalline solvent.The dipolar couplings obta
Celebre, G.,Luca, G. De,Longeri, M.,Catalano, D.,Lumetti, M.,Emsley, J.W.
p. 221 - 231
(2007/10/02)
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