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Original Articles

High Pressure Organometallic Chemistry : Diastereoselectivity in Diels Alder Reactions of 2,3-Dimethyl-1,3-Butadiene with (Z)-3-Tributyl-Stannylacrylic Acid (-) Menthyl Ester

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Pages 937-945 | Received 24 Feb 1987, Accepted 29 Sep 1987, Published online: 05 Dec 2006
 

Abstract

The effect of pressure (0.1 to 25OO MPa) on the asymmetric induction in the cycloaddition between (-)-menthyl 3-tributylstannyl-acrylate and 2,3-dimethyl-1,3-butadiene has been investigated under different solvent and temperature conditions. The high pressure considerably facilitates the addition but leads to a decrease or even an inversion of the diastereomeric excess. This behavior can be explained by a favored cisoid conformation of the ethylenic ester under high pressure.

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