138690-67-2Relevant academic research and scientific papers
Gold-catalyzed cyclization of allenyl acetal derivatives
Vasu, Dhananjayan,Pawar, Samir Kundlik,Liu, Rai-Shung
, p. 1751 - 1756 (2013/10/22)
The gold-catalyzed transformation of allenyl acetals into 5-alkylidenecyclopent-2-en-1-ones is described. The outcome of our deuterium labeling experiments supports a 1,4-hydride shift of the resulting allyl cationic intermediates because a complete deuterium transfer is observed. We tested the reaction on various acetal substrates bearing a propargyl acetate, giving 4-methoxy-5-alkylidenecyclopent-2-en-1-ones 4 via a degradation of the acetate group at the allyl cation intermediate.
Gold-catalyzed cyclization-cycloaddition cascade reactions of allenyl acetals with nitrones
Vasu, Dhananjayan,Liu, Rai-Shung
, p. 13638 - 13641 (2013/01/15)
Gold and silver: When allenyl acetals and nitrones are treated with a catalytic amount of a gold complex and a silver salt they react through a cyclization-cycloaddition cascade reaction to give a mixture of diastereomeric tricyclic products. The mixture converges to a single product upon acid hydrolysis (see scheme). The key intermediate is postulated to be a 1-methoxyfulvene species. Copyright
Asymmetric cyclopropanation by reaction of a γ-chloromethylated chiral vinylic sulfoxide with allylmagnesium bromide
Takemoto,Ohra,Sugiyama,Imanishi,Iwata
, p. 571 - 577 (2007/10/02)
An optically active vinylic sulfoxide bearing a leaving group at the γ-position was stereoselectively transformed into a chiral cyclopropane by means of a Michael addition with an allylmagnesinm bromide. The Michael induced ring-closure reaction requires both allylmagnesium bromide as a nucleophile and chloride as a leaving group for high diastereoselectivity. The absolute stereochemistry of the cycloadduct was confirmed by X-ray analysis.
