Showcasing research from Prof. Raphaël Robiette group at the Université catholique de Louvain, Belgium.
The Wittig reaction occupies a central role in organic synthesis as it is one of the most widely used methods for the synthesis of alkenes. It has however some limitations. Indeed, the synthesis of tetrasubstituted olefins by Wittig olefination is scarcely described in the literature; a Scifinder search revealing only three examples.
In collaboration with Janssen Pharmaceutical Companies of Johnson & Johnson, the group of Prof. Raphaël Robiette report in Org. Lett. the synthesis of tetrasubstitued olefins by Wittig reaction and a detailed study of factors that control the observed high stereoselectivity. This work provides an improved fundamental understanding of selectivity in the Wittig reaction (including a rationale for the observed decrease in selectivity for Wittig reactions of alpha-alkoxy aldehydes) and has considerable practical interest (stereoselective synthesis of tetrasubstituted olefins).
Details can be found in Org. Lett. 2017, 19, 1414-1417.