Dynamic Kinetic Resolution of 2-Phenylpropanal Derivatives to Yield β-Chiral Primary Amines via Bioamination.

Autor:	Fuchs, Christine S., Hollauf, Manuel, Meissner, Maximilian, Simon, Robert C., Besset, Tatiana, Reek, Joost N. H., Riethorst, Waander, Zepeck, Ferdinand, Kroutil, Wolfgang
Předmět:	PHENYLPROPANOIDS CHIRALITY AMINOTRANSFERASES AMINES ENANTIOSELECTIVE catalysis ENANTIOMERS METHYL ketones
Zdroj:	Advanced Synthesis & Catalysis; Jul2014, Vol. 356 Issue 10, p2257-2265, 9p
Abstrakt:	The amination of racemic α-chiral aldehydes, 2-phenylpropanal derivatives, was investigated employing ω-transaminases. By medium and substrate engineering the optical purity of the resulting β-chiral chiral amine could be enhanced to reach optical purities up to 99% ee. Using enantiocomplementary ω-transaminases allowed us to access the ( R)- as well as the ( S)-enantiomer in most cases. It is important to note that the stereopreference of the ω-transaminases found for α-chiral aldehydes did not correlate with the stereopreference previously observed for the amination of methyl ketones. In one case the stereopreference switched even upon exchanging a methyl substituent to a methoxy group. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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