From a racemate to a single enantiomer: Deracemization by stereoinversion

被引：154

作者：

Gruber, Christian C.

Lavandera, Ivan

Faber, Kurt

Kroutil, Wolfgang

机构：

[1] Graz Univ, Dept Chem Organ & Bioorgan Chem, A-8010 Graz, Austria

[2] Res Ctr Biocatalysis, Graz, Austria

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 14期

关键词：

alcohols; amines; amino acids; biotransformations; deracemization; stereoinversion;

D O I：

10.1002/adsc.200606158

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The stereoinversion of one enantiomer into its mirror-image counterpart within a racemate furnishes a single stereoisomeric product in 100% theoretical yield. This extremely efficient type of deracemization, whereby substrate and product possess an identical chemical structure, can be achieved by using bio- or chemo-catalysts or combinations thereof and is applicable to secondary alcohols, amines and cc-substituted carboxylic acids. Special emphasis is devoted to the theoretical background of the one-pot, single-step deracernization of sec-alcohols. 1 Introduction 2 Secondary Alcohols 2.1 Single-Step Deracernization 2.2 Two-Step Deracemization 3 alpha-Aryl- and alpha-Aryloxycarboxylic Acids 4 Chiral Amines and Amino Acids 4.1 Combining an Oxidase with a Chemical Reducing Agent 4.2 Multienzyme System 5 Chemical Methods 5.1 Enantioselective Protonation 5.2 Chiral Environment 6 Conclusions

引用

页码：1789 / 1805

页数：17

共 114 条

[1] A novel ruthenium catalysed deracemisation of alcohols [J].