Direct Enzymatic Route for the Preparation of Novel Enantiomerically Enriched Hydroxylated β-Amino Ester Stereoisomers

Forró, Enikő; Schönstein, László; Kiss, Lóránd; Vega‐Peñaloza, Alberto; Juaristi, Eusebio; Fülöp, Ferenc

doi:10.3390/molecules15063998

Cited by 12 publications

(12 citation statements)

References 34 publications

(34 reference statements)

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“…As in our earlier experiments, the racemic N-Boc-protected (tert-butoxycarbonyl) starting materials cis-and trans-2-aminocyclohex-3-enecarboxylic acid (1 and 16, respectively) were first regio-and stereoselectively hydroxylated by iodolactonization and lactone-opening procedures, as key steps resulting in the hydroxylated amino ester stereoisomers 2, 10, and 17. [9] The C-C double bond of all-cis-hydroxylated cyclohexene β-amino ester 2 derived from amino acid 1 (Scheme 1) was saturated first to give ethyl 5-hydroxy-2-aminocyclohexanecarboxylate 3. Amino ester 3 was then subjected to hydroxy-fluorine exchange by using different fluorinated organic reagents.…”

Section: Resultsmentioning

confidence: 99%

Selective Synthesis of New Fluorinated Alicyclic β‐Amino Ester Stereoisomers

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Section: Resultsmentioning

confidence: 99%

Selective Synthesis of New Fluorinated Alicyclic β‐Amino Ester Stereoisomers

et al. 2011

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“…64 Starting from 1,4-cyclohexadiene-or 1,3-cyclohexadienederived bicyclic lactams, the above methodology based on iodolactonization, HI elimination, and subsequent lactone ringopening was successfully used for the synthesis of other hydroxylated β-aminocyclohexenecarboxylates ( Figure 16). 64,65 The ring C−C double bond of hydroxylated cyclic β-amino acids offers a possibility for further selective functionalizations, leading to the synthesis of different highly functionalized bioactive compounds. Thus, all-cis-methyl 5-hydroxy-2-aminocyclohexenecarboxylate was used as a precursor in the synthesis of the antibiotic Fortamycine.…”

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Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

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Introduction 1116 2. Carbocyclic β-Amino Acids 1118 2.1. Syntheses of Five-or Six-Membered Carbocyclic β-Amino Acids 1118 2.1.1. Carbocyclic β-Amino Acids from β-Keto Esters 1119 2.1.2. Carbocyclic β-Amino Acids by Metathesis 1119 2.1.3. Carbocyclic β-Amino Acids by Amino Group Conjugate Addition 1122 2.1.4. Carbocyclic β-Amino Acids by Cycloaddition 1124 2.1.5. Carbocyclic β-Amino Acids by Desymmetrization of meso-Anhydrides 1124 2.1.6. Carbocyclic β-Amino Acids from Natural Sources 1125 2.1.7. Miscellaneous 1127 2.2. Syntheses of Small-Ring Carbocyclic β-Amino Acids 1128 2.3. Syntheses of Carbocyclic β-Amino Acids with Larger Ring Systems 1129 2.4. Synthesis of Functionalized Carbocyclic β-Amino Acids 1131 2.4.1. Syntheses of Functionalized Cyclic β-Amino Acids by C−C Double Bond Functionalization 1131 2.4.2. Several Relevant Routes to Functionalized Cyclic β-Amino Acids Other Than Functionalization of the Ring C−C Double Bond 1137 3. Cyclic β-Amino Acids with a Heteroatom in the Ring 1137 3.1. Syntheses of Cyclic β-Amino Acids with a N Atom in the Ring 1138 3.1.1. Three-and Four-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.2. Five-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.3. Six-Membered N-Containing Cyclic β-Amino Acids 1145 3.1.4. N-Containing Cyclic β-Amino Acids with Larger Ring Systems 1148 3.2. Syntheses of Cyclic β-Amino Acids with an O Atom in the Ring 1148 3.2.1. Four-Membered O-Containing Cyclic β-Amino Acids 1148 3.2.2. Five-Membered O-Containing Cyclic β-Amino Acids 1149 3.2.3. Six-Membered O-Containing Cyclic β-Amino Acids 1155 3.3. Cyclic β-Amino Acids with Other Heteroatoms in the Ring 1159 4. Some Relevant Biological Properties of Cyclic β-Amino Acids 1160 4.1. Cyclic β-Amino Acids Possessing Antifungal or Antibacterial Properties 1160 4.2. Antiviral Cyclic β-Amino Acids 1162 4.3. Cyclic β-Amino Acids with Antitumoral Properties 1162 4.4. Cyclic β-Amino Acids with Cardioprotective

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“…CO Lactone opening with NaOEt furnished three hydroxylated amino ester stereoisomers, 97, 98 and 101 (Scheme 27). 103 Epimerization was also observed in the case of cis-lactone 96, because of the presence of base in the reaction mixture (NaOEt, see section 3.3).…”

Section: Synthesis Of Racemic and Enantiomerically Pure Starting Matementioning

confidence: 99%

“…These -amino ester carboxylates 94a-d were prepared by well-known methods, starting from cyclopentadiene and cyclohexadienes (92a-c). 102,103 In the first step, bicyclic -lactams 93a-c…”

Section: Synthesis Of Racemic and Enantiomerically Pure Starting Matementioning

confidence: 99%

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Selective functionalization of alicyclic beta-amino acids by 1,3-dipolar cycloaddition of nitrile oxides

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Direct Enzymatic Route for the Preparation of Novel Enantiomerically Enriched Hydroxylated β-Amino Ester Stereoisomers

Cited by 12 publications

References 34 publications

Selective Synthesis of New Fluorinated Alicyclic β‐Amino Ester Stereoisomers

Selective Synthesis of New Fluorinated Alicyclic β‐Amino Ester Stereoisomers

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

Selective functionalization of alicyclic beta-amino acids by 1,3-dipolar cycloaddition of nitrile oxides

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