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Efficient Asymmetric Synthesis of 1‐Cyano‐tetrahydroisoquinolines from Lipase Dual Activity and Opposite Enantioselectivities in α‐Aminonitrile Resolution
Author(s) -
Sakulsombat Morakot,
Vongvilai Pornrapee,
Ramström Olof
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402615
Subject(s) - dual (grammatical number) , lipase , resolution (logic) , chemistry , computer science , organic chemistry , art , enzyme , literature , programming language
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.