Abstract
AbstractThe mechanism and origin of high E selectivity in the modified Julia olefination of aromatic aldehydes have been explored by computational and experimental means. Reversibility of addition and hence selectivity of the formation of sulfinate 5 is very variable and depends on the nature of the sulfone substrate. However, in all cases, elimination occurs through a concerted antiperiplanar and synperiplanar mechanism for sulfinates anti‐5 and syn‐5, respectively. Both syn and anti diastereomeric pathways thus lead preferentially to the (E)‐alkene.
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