| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348158 | Tetrahedron: Asymmetry | 2006 | 11 Pages |
Under very mild conditions, biotransformations of racemic azido nitriles using Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, afforded highly enantiopure, (R)-α-arylmethyl- and (+)-α-cyclohexylmethyl-β-azidopropanoic acids and their (S)- and (−)-carboxamide derivatives in excellent yields. The resulting functionalized chiral organoazides were converted in a straightforward fashion to a pair of antipodes of α-benzyl-β-amino acids (R)-13 and (S)-13. Azido carboxamide (S)-11a and azido carboxylic acid (R)-12a underwent ‘click’ reactions with diethyl acetylenedicarboxylate and phenylacetylene to produce functionalized chiral triazoles 14 and 15, respectively. The easy preparation of the starting nitrile substrates, highly efficient and enantioselective biotransformation reactions, and versatile utility of the resulting functionalized azido carboxylic acids and amide derivatives, render this method very attractive and practical in organic synthesis.
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(S)-(−)-3-Azido-2-(4-methoxyphenylmethyl)propionamideC11H14N4O2Ee >99%[α]D25=-29.9 (c 1.625, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(S)-(−)-3-Azido-2-benzylpropionamideC10H12N4OEe >99%[α]D25=-31.9 (c 2.950, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R)-(−)-3-Azido-2-benzylpropionic acidC10H11N3O2Ee >99%[α]D25=-29.0 (c 2.000, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(R)-(−)-3-Azido-2-(4-methylphenylmethyl)propionic acidC11H13N3O2Ee >99%[α]D25=-34.0 (c 2.705, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S)-(−)-3-Azido-2-(4-fluorophenylmethyl)propionamideC10H11N4OFEe >99%[α]D25=-34.5 (c 2.495, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R)-(−)-3-Azido-2-(4-fluorophenylmethyl)propionic acidC10H10N3O2FEe >99%[α]D25=-27.3 (c 2.125, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S)-(−)-3-Azido-2-(4-chlorophenylmethyl)propionamideC10H11N4OClEe = 86.7%[α]D25=-29.2 (c 1.370, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R)-(−)-3-Azido-2-(4-chlorophenylmethyl)propionic acidC10H10N3O2ClEe >99%[α]D25=-24.6 (c 1.055, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S)-(−)-3-Azido-2-(3-chlorophenylmethyl)propionamideC10H11N4OClEe >99%[α]D25=-33.6 (c 1.250, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R)-(−)-3-Azido-2-(3-chlorophenylmethyl)propionic acidC10H10N3O2ClEe >99%[α]D25=-31.8 (c 1.130, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S)-(−)-3-Azido-2-(2- chlorophenylmethyl)propionamideC10H11N4OClEe >99%[α]D25=-39.6 (c 2.575, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R)-(−)-3-Azido-2-(2-chlorophenylmethyl)propionic acidC10H10N3O2ClEe >99%[α]D25=-29.4 (c 2.855, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S)-(−)-3-Azido-2-(4-bromophenylmethyl)propionamideC10H11N4OBrEe >99%[α]D25=-29.1 (c 1.445, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R)-(−)-3-Azido-2-(4-bromophenylmethyl)propionic acidC10H10N3O2BrEe = 93.6%[α]D25=-29.5 (c 1.220, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S∗)-(−)-3-Azido-2-cyclohexylmethylpropionamideC10H18N4OEe >99%[α]D25=-28.2 (c 2.800, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R∗)-(+)-3-Azido-2-cyclohexylmethylpropionic acidC10H17N3O2Ee = 95.6%[α]D25=+6.0 (c 4.300, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S∗)-(−)-3-Azido-2-cyclopropylmethylpropionamideC7H12N4OEe = 83.0%[α]D25=-29.8 (c 1.945, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R∗)-3-Azido-2-cyclopropylmethylpropionic acidC7H11N3O2Ee = 58.6%[α]D25=0 (c 2.800, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S∗)-(−)-2-AzidomethylpentanamideC6H12N4OEe = 65.0%[α]D25=-12.2 (c 1.880, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R∗)-(−)-2-Azidomethylpentanoic acidC6H11N3O2Ee = 75.0%[α]D25=-2.6 (c 1.175, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(R)-(−)-3-Azido-2-(4- methoxyphenylmethyl)propionic acidC11H13N3O3Ee >99%[α]D25=-38.2 (c 2.010, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S)-(−)-3-Amino-2-benzylpropionic acidC10H13NO2Ee >99%[α]D25=-17.3 (c 1.850, 1 M HCl)Source of chirality: enzymatic synthesisAbsolute configuration: S
(S)-(−)-Diethyl 1-[(2-carbamoyl-3-phenyl)propyl]-1H-[1,2,3]triazole-4,5-dicarboxylateC18H22N4O5Ee >99%[α]D25=-72.6 (c 1.350, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
(R)-(+)-1-[(2-hydroxycarbonyl-3-phenyl)propyl]-4-phenyl-1H-[1,2,3]triazoleC18H17N3O2Ee >99%[α]D25=-7.2 (c 1.955, MeOH)Source of chirality: enzymatic synthesisAbsolute configuration: R
(S)-(−)-3-Azido-2-(4-methylphenylmethyl)propionamideC11H14N4OEe >99%[α]D25=-34.9 (c 2.980, CHCl3)Source of chirality: enzymatic synthesisAbsolute configuration: S
