Efficient asymmetric hydrogenation of the C-C double bond of 2-methyl- and 2,3-dimethyl-N-phenylalkylmaleimides by Aspergillus fumigatus.

MAXIMILANO SORTINO; SUSANA ZACCHINO

TETRAHEDRON-ASYMMETRY

PERGAMON-ELSEVIER SCIENCE LTD

Año: 2010 vol. 21 p. 535 - 539

0957-4166

Eight N-phenylalkylmaleimides (four 2-methyl-N-phenylalkylmaleimides and four 2,3-dimethyl-Nphenylalkylmaleimides with an alkyl chain (CH2)n (n = 1–4) between the imide N and the benzene ring) were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. with an alkyl chain (CH2)n (n = 1–4) between the imide N and the benzene ring) were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. N-phenylalkylmaleimides (four 2-methyl-N-phenylalkylmaleimides and four 2,3-dimethyl-Nphenylalkylmaleimides with an alkyl chain (CH2)n (n = 1–4) between the imide N and the benzene ring) were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. 2)n (n = 1–4) between the imide N and the benzene ring) were subjected to biotransformation using the fungal strain Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. Aspergillus fumigatus ATCC 26934. All compounds were reduced enantioselectively to their respective succinimides: (R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. R)-2-methyl-N-phenylalkylsuccinimides and (2R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. R,3R)-2,3-dimethyl-N-phenylalkylsuccinimides, with satisfactory conversion rates and high stereoisomeric excesses. NMR analysis using the chiral shift reagent Eu(hfc)3 showed that enantiomeric excesses were >99%. excesses were >99%. 3 showed that enantiomeric excesses were >99%.