A Straightforward Deracemization of sec-Alcohols Combining Organocatalytic Oxidation and Biocatalytic Reduction

被引：27

作者：

Liardo, Elisa ^{[1
]}

Rios-Lombardia, Nicolas ^{[2
]}

Moris, Francisco ^{[2
]}

Gonzalez-Sabin, Javier ^{[2
]}

Rebolledo, Francisca ^{[1
]}

机构：

[1] Univ Oviedo, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain

[2] EntreChem SL, Vivero Ciencias Salud, Oviedo 33011, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 23期

基金：

欧盟地平线“2020”;

关键词：

Alcohols; Organocatalysis; Oxidation; Oxidoreductases; SECONDARY ALCOHOLS; ONE-POT; KINETIC RESOLUTION; LIGANDS; DERACEMISATION; STEREOINVERSION; ORGANOBORANES; APREPITANT; CATALYSTS; PYRIDINE;

D O I：

10.1002/ejoc.201800569

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98%). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95% yield, >99% ee, >99: < 1 dr).

引用

页码：3031 / 3035

页数：5

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