The carene class of natural products has garnered much interest due to its bicyclo[4.1.0]heptane skeleton. F�rstner and Hannen have reported synthesis of bicyclo[4.1.0]heptane skeletons starting from acyclic propargyl acetate precursors via a gold-catalyzed reaction (F�rstner, A; Hannen, P. Chem. Eur. J. 2006  , 12, 3006). The reaction takes place with high regio- and stereocontrol, however little is known about the mechanism by which this rearrangement occurs. Using quantum chemical methods (density functional theory), we investigate the mechanism of this Ohloff-Rautenstrauch reaction.

Density functional theory investigation of the mechanism for AuCl<sub>3</sub>-catalyzed conversion of acyclic propargyl acetates to bicyclo[4.1.0]heptane carbocycles

247th National Meeting (2014)

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Density functional theory investigation of the mechanism for AuCl3-catalyzed conversion of acyclic propargyl acetates to bicyclo[4.1.0]heptane carbocycles

Density functional theory investigation of the mechanism for AuCl₃-catalyzed conversion of acyclic propargyl acetates to bicyclo[4.1.0]heptane carbocycles