BioChem - DOS

Asymmetric Amination of Tetralone and Chromanone Derivatives Employing ω-Transaminases

ACS catalysis

Pressnitz, Desiree; Fuchs, Christine S.; Sattler, Johann H.; Knaus, Tanja; Macheroux, Peter; Mutti, Francesco G.; Kroutil, Wolfgang

<P>Various (<I>S</I>)-selective and (<I>R</I>)-selective &omega;-transaminases were investigated for the amination of 1- and 2-tetralone and derivatives as well as of 3- and 4-chromanone. All ketones tested were aminated to give the corresponding enantiopure amines (<I>ee</I> > 99%) employing at least one of the enzymes investigated. In most of the cases the (<I>S</I>)- as well as the (<I>R</I>)-enantiomer was obtained in optically pure form. The amination of 3-chromanone was performed on a 100 mg scale leading to optically pure (<I>R</I>)-3-aminochromane (<I>ee</I> > 99%) with complete conversion and 78% isolated yield.</P><P><B>Graphic Abstract</B><BR><IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/accacs/2013/accacs.2013.3.issue-4/cs400002d/production/images/medium/cs-2013-00002d_0003.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/cs400002d'>ACS Electronic Supporting Info</A></P>

2013

American Chemical Society

2155-5435

3

4

pp.555-559

10.1021/cs400002d

http://click.ndsl.kr/servlet/OpenAPIDetailView?keyValue=05787966&target=NART&cn=NART65756271

asymmetric catalysis; biocatalysis; amination; ω-transaminase; aminochromane; aminotetraline