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Rh-catalyzed asymmetric hydroformylation of heterocyclic olefins using chiral diphosphite ligands. Scope and
Javier Mazuela1, Mercedes Coll, Oscar Pàmies
1Departament de Química Física i Inorgànica, Universitat Rovira i Virgili, Campus Sescelades, C/ Marcel.lí Domingo, s/n 43007 Tarragona, Spain.
Abstract:
We used a series of diphosphite ligands to study the effect of the ligand backbone, the length of the bridge, and the substituents of the biphenyl moieties and determine the scope of this type of ligand in the Rh-catalyzed asymmetric hydroformylation of several hetereocylic olefins. By carefully selecting the ligand components, we achieved high chemo-, regio-, and enantioselectivities in different substrate types. Unprecedentedly high enantioselectivities for five-membered heterocyclic olefins were therefore obtained. Note that both enantiomers of the hydroformylation products can be synthesized using the same ligand by a simple substrate change. For the seven-membered heterocyclic dioxepines, our results are among the best obtained. Also, both enantiomers of the hydroformylation products can be obtained by using pseudoenantiomer ligands or by carefully tuning the ligand parameters.
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