Gold(I)-catalyzed intermolecular hydroalkoxylation of allenes: A DFT study

The mechanistic and regiochemical aspects in the Au(I)-catalyzed intermolecular hydroalkoxylation of allenes have been studied computationally. The most favorable pathway is nucleophilic attack of an Au(I)-coordinated allene, which occurs irreversibly. An Au(I)-catalyzed mechanism is proposed that allows the facile interconversion of regioisomeric allylic ether products. The regioisomers are connected via a stabilized diether intermediate with a C-Au σ-bond, which successfully explains the observed regioselectivity for the thermodynamic product.

Gold(I)-catalyzed intermolecular hydroalkoxylation of allenes: A DFT study

R. S. Paton, F. Maseras

Org. Lett. 2009, 11, 2237-2240

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