Highly enantiomeric hydrogenation of C-C double bound of methylated N-phenyl and N-phenylalkylmaleimides by Aspergillus fumigatus

MAXIMILANO SORTINO; SUSANA ZACCHINO

Practical Methods for Biocatalysis and Biotransformations 2

John Wiley & son

Año: 2012; p. 108 - 114

Biocatalysis has become an increasingly valuable tool for the easy preparation of chiral compounds, which are greatly needed in organic synthesis as well as in the pharmaceutical and agrochemical fields, due to the great differences observed in the biological activity of stereoisomers (enantiomers and diastereoisomers). Whole fungal cells grow rapid in natural and synthetic media, are ease of handling, and simple scale-up. They play a leading role in chemo-enzymatic syntheses because of their great diversity which produces a range of useful enzymes with catalytic abilities. 2-Methyl-N-phenyl- and 2,3-dimethyl-N-phenylmaleimides have proven to be good substrates for biocatalytic C-C double bond reduction leading to the introduction of one or two stereogenic centers into an achiral structure with high enantioselectivity. This biocatalytic process has been performed using plant cells (Nicotiana tabacum, Cinechococcus sp., and Marchantia polymorpha) as well as fungal strains (Aspergillus flavus, A. fumigatus, and A. niger). Then, A. fumigatus has been used to enantiomerically hydrogenate 2-methyl- and 2,3-dimethyl- N-phenylalkylmaleimides with an alkyl chain ranging 1 to 4 atoms of carbon.