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Efficient asymmetric synthesis of 1-cyano-tetrahydroisoquinolines from lipase dual activity and opposite enantioselectivities in ?-Aminonitrile resolution.

ABSTRACT: Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic ?-aminonitrile compounds are described. ?-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, where opposite enantioselectivities could be recorded for certain substrates.

SUBMITTER: Sakulsombat M

PROVIDER: S-EPMC4497319 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Efficient asymmetric synthesis of 1-cyano-tetrahydroisoquinolines from lipase dual activity and opposite enantioselectivities in α-Aminonitrile resolution.

Sakulsombat Morakot M Vongvilai Pornrapee P Ramström Olof O

Chemistry (Weinheim an der Bergstrasse, Germany) 20140723 36

Dual promiscuous racemization/amidation activities of lipases leading to efficient dynamic kinetic resolution protocols of racemic α-aminonitrile compounds are described. α-Amidonitrile products of high enantiomeric purity could be formed in high yields. Several lipases from different sources were shown to exhibit the dual catalytic activities, where opposite enantioselectivities could be recorded for certain substrates. ...[more]

PMID: 25055970

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