Straightforward preparation of biologically active 1-aryl- and 1-heteroarylpropan-2-amines in enantioenriched form

被引：30

作者：

Rodriguez-Mata, Maria ^{[1
,2
]}

Gotor-Fernandez, Vicente ^{[1
,2
]}

Gonzalez-Sabin, Javier ^{[3
]}

Rebolledo, Francisca ^{[1
,2
]}

Gotor, Vicente ^{[1
,2
]}

机构：

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

[2] Univ Oviedo, Inst Univ Biotecnol Asturias, E-33006 Oviedo, Spain

[3] Entrechem SL, Oviedo 33006, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 07期

关键词：

DYNAMIC KINETIC RESOLUTION; BIOCATALYTIC ROUTES; AMINES; HISTAMINE; LIPASE; ENANTIOMERS; DERIVATIVES; COMPLEX; POTENT; RAT;

D O I：

10.1039/c0ob00800a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Because of the importance of developing stereoselective syntheses for single enantiomers, a selected panel of racemic biologically active 1-aryl- and 1-heteroarylpropan-2-amines has been prepared, followed by a study of their behavior in enzymatic kinetic resolution (KR) processes. For this purpose, lipase B from Candida antarctica (CAL-B) proved to be an ideal biocatalyst allowing the preparation of the corresponding enantioenriched (R)-amides and (S)-amines by aminolysis reactions. Likewise, dynamic kinetic resolutions (DKR) have been successfully achieved combining the use of CAL-B and Shvo's catalyst. This research constitutes the first example of a lipase-catalyzed DKR process of beta-substituted isopropylamines.

引用

页码：2274 / 2278

页数：5

共 46 条

[1] First dynamic kinetic resolution of selenium-containing chiral amines catalyzed by palladium (Pd/BaSO4) and Candida antartica lipase (CAL-B) [J].