Arylmagnesium bromide additions to 1-tetralone-2-acetic acid followed by catalytic hydrogenolysis: stereochemical consequences
C Djerassi, GR Pettit, DL Herald…
Index: Djerassi, Carl; Pettit, George R.; Herald, Delbert L.; Sanson, Dale R. Journal of Organic Chemistry, 1991 , vol. 56, # 18 p. 5360 - 5368
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Abstract
The infrared spectrum of the product showed the characteristic y-lactone carbonyl band at 5.65 pM. The stereochemical configuration of the lactone ring 2a was subsequently established as cis by X-ray crystallographic structure determination (Figure 1). Several attempts to vary the reaction time and temperature of this inverse Grignard reaction resulted in an optimum yield of only 25% due to competitive reaction with the ester. Catalytic ...
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