English
Enantioselective synthesis of (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol by Candida antarctica lipase B
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Key words:
- N-(Benzylcarbamoyl)-4-aminocyclopent-2-
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[19] Compound 2: 1H NMR (400 MHz, CDCl3): δ 7.47-7.09 (m, 5H), 5.97 (m, 2H), 5.55 (s, 1H), 5.11 (s, 2H), 4.85 (m, 1H), 4.76 (m, 1H), 2.84 (m, 1H), 2.30 (t, 2H), 1.56 (m, 1H), 1.17 (t, 3H). Compound 3: 1H NMR (400 MHz, CDCl3): d 7.61-7.24 (m, 5H), 5.98 (m, 2H), 5.55 (s, 1H), 5.11 (s, 2H), 4.83 (m, 1H), 4.69 (m, 1H), 2.97-2.65 (m, 1H), 2.29 (t, 2H), 1.70-1.48 (m, 3H), 0.98 (t, 3H). Compound 4: 1H NMR (400 MHz, CDCl3): δ 7.94-7.13 (m, 10H), 6.01 (m, 2H), 5.72 (s, 1H), 5.11 (s, 2H), 4.85(m, 1H), 4.75 (m, 1H), 2.97-2.85 (m, 1H), 1.65 (m, 1H).[19] Compound 2: 1H NMR (400 MHz, CDCl3): δ 7.47-7.09 (m, 5H), 5.97 (m, 2H), 5.55 (s, 1H), 5.11 (s, 2H), 4.85 (m, 1H), 4.76 (m, 1H), 2.84 (m, 1H), 2.30 (t, 2H), 1.56 (m, 1H), 1.17 (t, 3H). Compound 3: 1H NMR (400 MHz, CDCl3): d 7.61-7.24 (m, 5H), 5.98 (m, 2H), 5.55 (s, 1H), 5.11 (s, 2H), 4.83 (m, 1H), 4.69 (m, 1H), 2.97-2.65 (m, 1H), 2.29 (t, 2H), 1.70-1.48 (m, 3H), 0.98 (t, 3H). Compound 4: 1H NMR (400 MHz, CDCl3): δ 7.94-7.13 (m, 10H), 6.01 (m, 2H), 5.72 (s, 1H), 5.11 (s, 2H), 4.85(m, 1H), 4.75 (m, 1H), 2.97-2.85 (m, 1H), 1.65 (m, 1H).
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[20] L. Werner, J.R. Hudlicky, M. Wernerova, et al., Synthesis of 1,2-and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines, Tetrahedron 66 (2010) 3761-3769.[20] L. Werner, J.R. Hudlicky, M. Wernerova, et al., Synthesis of 1,2-and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines, Tetrahedron 66 (2010) 3761-3769.
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[21] Analytical HPLC methods: the enantiomeric excess analysis was performed using a HPLC system (Shimadzu, Japan) equipped with a CHIRALPAK IF column (0.46 mm × 250 mm × 5 mm), elution with ethanol/hexane 15:85 v/v for compound 1, ethanol/hexane 25:75 v/v for compounds 2 and 3, ethanol/hexane 30:70 for compound 4.[21] Analytical HPLC methods: the enantiomeric excess analysis was performed using a HPLC system (Shimadzu, Japan) equipped with a CHIRALPAK IF column (0.46 mm × 250 mm × 5 mm), elution with ethanol/hexane 15:85 v/v for compound 1, ethanol/hexane 25:75 v/v for compounds 2 and 3, ethanol/hexane 30:70 for compound 4.
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