由α-氨基酸衍生的手性硫脲催化的中环酸酐的对映选择性甲醇解合成非对映异构体的半酯。

Synthesis of both enantiomers of hemiesters by enantioselective methanolysis of meso cyclic anhydrides catalyzed by alpha-amino acid-derived chiral thioureas.

机构信息

Instituto CINQUIMA and Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain.

出版信息

J Org Chem. 2010 Aug 6;75(15):5417-20. doi: 10.1021/jo100792r.

DOI:10.1021/jo100792r

PMID:20586496

Abstract

Both ureas and thioureas derived from L- or D-valine act as bifunctional organocatalysts able to induce the enantioselective alcoholysis of mono-, bi-, and tricyclic meso anhydrides. The desymmetrization occurs in near quantitative yields and excellent enantiomeric ratios (up to >99:<1) under low catalyst loading. Both enantiomers of the hemiesters can be directly obtained by changing the configuration of the catalyst.

摘要

由 L-或 D-缬氨酸衍生的脲和硫脲均可作为双功能有机催化剂，诱导单环、双环和三环内酸酐的对映选择性醇解。在低催化剂负载下，不对称化以接近定量的收率和极好的对映体比（高达>99:<1）发生。通过改变催化剂的构型，可以直接获得半酯的两种对映异构体。