ChemInform Abstract: Chelation Control Through the Coordination of Lewis Acids to an Acetylenic π-Bond.
Abstract
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ChemInform Abstract
The chemo- and regioselectivity of chelation-controlled reductions of aromatic aldehydes are studied by competition experiments. It is found that various Lewis acids coordinate to π-electrons of the C—C triple bond and to the aldehyde oxygen in a bidentate manner, and thus enhance the reactivity of ortho-alkynyl substituted aldehydes in comparison to para-alkynyl substituted analogues toward reduction. The chelation effect is also observed for cyclohexanecarbaldehyde (XI) and for dialdehyde (XIV).
