Tellurium in organic synthesis: the enantioselective synthesis of the pheromone blend components of Mayetiola destructor, Drosophila mulleri and Contarinia pisi

Ferrarini, Renan S.; Comasseto, J. V.; Santos, Alcindo A. Dos

doi:10.1016/j.tetasy.2009.08.003

Cited by 12 publications

References 39 publications

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Preparative Uses of Organoselenium and Organotellurium Compounds

Nomoto

2011

Patai's Chemistry of Functional Groups

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Organoselenium and organotellurium compounds are important not only for synthetic organic chemistry but also materials science or pharmacology. Attentions are mainly focused on the reactivity of selenium and tellurium reagents on electrophilic, nucleophilic, radical, transition‐metal‐catalyzed, reduction, and oxidation reaction. Organoselenium and organotellurium have unique reactivities, and their radical reactions and the transition‐metal‐catalyzed reactions have been developed recently. This chapter deals with the recent advances in the preparative uses of organoselenium and organotellurium compounds.

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Preparative Uses of Organoselenium and Organotellurium Compounds

Nomoto

2011

Patai's Chemistry of Functional Groups

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Stereoselective Bioreduction of Telluro‐Acetophenones to Optically Active Hydroxy Tellurides

2020

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Organotellurium compounds exhibit a broad range of useful applications in organic synthesis, materials science and medicinal chemistry fields. Despite their increasing applicability, the synthesis of enantiomerically pure organotellurium compounds remains nowadays scarcely reported in the literature. Herein, the chemical synthesis and biocatalyzed reductions of a set of telluro‐acetophenones using both (R) and (S)‐selective alcohol dehydrogenases (ADHs) is described for the first time, obtaining enantiomerically enriched hydroxy tellurides with excellent selectivities under very mild reaction conditions. On the one hand, enantiopure para‐substituted (S)‐hydroxy tellurides were obtained using the Ras‐ADH (77–95 % conversion) and ADH‐A (52–75 %), the ADH‐A leading to the enantiopure (S)‐hydroxy tellurides substituted at the meta‐position (69–75 %). On the other hand, the evo‐1.1.200 displayed high selectivity towards the preparation of optically alcohols with substitutions at the para‐position of the aromatic ring (60–68 % conversion and 92–97 % ee), while the Lb‐ADH led to the best results when reducing bulky ketones at the meta‐position (79–82% conversion and 88–99 % ee).

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