135468-06-3Relevant academic research and scientific papers
Gold-Catalyzed stereocontrolled synthesis of 2,3-Bis(acetoxy)-1,3-dienes
Huang, Xiaogen,De Haro, Teresa,Nevado, Cristina
supporting information; experimental part, p. 5904 - 5908 (2010/03/03)
A 1,4-bis(propargyl acetates) undergo a highly selective tandem 1,2-/1,2-Bis(acetoxy) migration to give 2,3-Bis(acetoxy)-1,3-dienes, that, depending on the catalyst of choice,(1Z,3Z) or (1Z,3E and 1E,3Z)-1,3-dienes can be obtained in a stereocontrolled manner. It was found that the 1,2-Bis(acetoxy) migration was favored in all studied cases and no allene product was observed in the reaction mixtures. It was also found that more e sterically demanding substrate dramatically improved the selectivity thereby revealing the key role of sterics in the stereocontrol of these transformations. The results show that the choice of the acetoxy migrating first seemed to be of key importance and is determined both by the electronic character and sterical bulkiness of substituents at the propargylic position.
