The stereochemistry of the vinylogous peterson elimination
Abstract
The base-catalysed eliminations of the vinylogous β-hydroxysilanes 7, 9, 11 and 12 are stereospecifically syn, giving largely the trans,trans-diene 8 from 7 and 11, the cis,trans-diene 10 from 9, and the trans,cis-diene 13 from 12; when a cis double bond is produced, it is selectively placed adjacent to the carbon atom that originally carried the hydroxy group.