| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348107 | Tetrahedron: Asymmetry | 2012 | 8 Pages |
A simple chemoenzymatic method for the preparation of optically active (5-aryltetrazolyl-2)-4-butan-2-ol, (5-aryltetrazolyl-2)-propan-2-ol, and their acetates has been developed. The starting compounds (5-aryltetrazolyl-2)-4-butan-2-one and (5-aryltetrazolyl-2)-propan-2-one were obtained by a Michael-type addition of 5-aryl substituted tetrazoles to methyl vinyl ketone, and alkylation of 5-aryl substituted tetrazoles with chloroacetone, respectively. Their reduction with sodium borohydride afforded racemic mixtures of (5-aryltetrazolyl-2)-4-butan-2-oles and (5-aryltetrazolyl-2)-propan-2-oles.
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(S)-(+)-(5-(2-Chlorophenyl)tetrazolyl-2)-4-butan-2-olC11H13ClN4OEe = 98%[α]D24=+22.2 (c 2.12, CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (S)
(R)-(−)-(5-Phenyltetrazolyl-2)-4-butan-2-yl acetateC13H16N4O2Ee = 96%[α]D22=-22.6 (c 2.19, CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(−)-(5-(4-Methylphenyl)tetrazolyl-2)-4-butan-2-yl acetateC14H18N4O2Ee = 93%[α]D22=-20.2 (c 2.35, CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(−)-(5-(4-Chlorophenyl)tetrazolyl-2)-4-butan-2-yl acetateC13H15ClN4O2Ee = 91%[α]D22=-24.9 (c 2.38, CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(−)-(5-(2-Chlorophenyl)tetrazolyl-2)-4-butan-2-yl acetateC13H15ClN4O2Ee = 80%[α]D24=-16.7 (c 3, CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(−)-(5-Phenyltetrazolyl-2)-4-butan-2-olC11H14N4OEe = 96%[α]D28=-29.7 (c 1.60, CH3OH)Source of chirality: chemical hydrolysis of optically active esterAbsolute configuration: (R)
(R)-(−)-(5-(4-Methylphenyl)tetrazolyl-2)-4-butan-2-olC12H16N4OEe = 93%[α]D22=-25.6 (c 1.76, CH3OH)Source of chirality: chemical hydrolysis of optically active esterAbsolute configuration: (R)
(R)-(−)-(5-(4-Chlorophenyl)tetrazolyl-2)-4-butan-2-olC11H13ClN4OEe = 92%[α]D22=-22.95 (c 1.22, CH3OH)Source of chirality: chemical hydrolysis of optically active esterAbsolute configuration: (R)
(S)-(+)-(5-(4-Chlorophenyl)tetrazolyl-2)-propan-2-olC10H11ClN4OEe = 74%[α]D26=+34.5 (c 2.42, CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (S)
(S)-(+)-(5-(2-Chlorophenyl)tetrazolyl-2)-propan-2-olC10H11ClN4OEe = 99%[α]D25=+43.1 (c 1.95, CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (S)
(R)-(+)-(5-(4-Methylphenyl)tetrazolyl-2)-propan-2-yl acetateC13H16N4O2Ee = 83%[α]D29=+7.3 (c 2.18, CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(+)-(5-(4-Chlorophenyl)tetrazolyl-2)-propan-2-yl acetateC12H13ClN4O2Ee = 91%[α]D26=+5.2 (c 2.31, CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(+)-(5-(2-Chlorophenyl)tetrazolyl-2)-propan-2-yl acetateC12H13ClN4O2Ee = 78%[α]D26=+8.8 (c 2.85 CH3OH)Source of chirality: enzymatic kinetic resolutionAbsolute configuration: (R)
(R)-(−)-(5-(4-Methylphenyl)tetrazolyl-2)-propan-2-olC11H14N4OEe = 83%[α]D26=-52.0 (c 1.50, CH3OH)Source of chirality: chemical hydrolysis of optically active esterAbsolute configuration: (R)
