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Stereoselective Bioreduction of Telluro-Acetophenones to Optically Active Hydroxy Tellurides

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논문

Stereoselective Bioreduction of Telluro-Acetophenones to Optically Active Hydroxy Tellurides

학술지

European journal of organic chemistry

저자명

Bandeira, Pamela Taisline; Gotor‐ Ferná ndez, Vicente; Piovan, Leandro

초록

<P>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&#8208;acetophenones using both (<I>R</I>) and (<I>S</I>)&#8208;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 <I>para</I>&#8208;substituted (<I>S</I>)&#8208;hydroxy tellurides were obtained using the Ras&#8208;ADH (77&ndash;95 % conversion) and ADH&#8208;A (52&ndash;75 %), the ADH&#8208;A leading to the enantiopure (<I>S</I>)&#8208;hydroxy tellurides substituted at the <I>meta</I>&#8208;position (69&ndash;75 %). On the other hand, the evo&#8208;1.1.200 displayed high selectivity towards the preparation of optically alcohols with substitutions at the <I>para</I>&#8208;position of the aromatic ring (60&ndash;68 % conversion and 92&ndash;97 % <I>ee</I>), while the Lb&#8208;ADH led to the best results when reducing bulky ketones at the <I>meta</I>&#8208;position (79&ndash;82% conversion and 88&ndash;99 % <I>ee</I>).</P>

발행연도

2020

ISSN

1434-193x

ISSN

1099-0690

2020

9

페이지

pp.1129-1135

주제어

Alcohol dehydrogenases; Asymmetric synthesis; Enzyme catalysis; Optically active organotellurides; Tellurium

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논문; 2020-02-19

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