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Dehaloperoxidase Catalyzed Stereoselective Synthesis of Cyclopropanol Esters
Siriboe, Mary G ; Vargas, David A ; Fasan, Rudi JOC,2022,88(12):7630-7640. DOI: 10.1021/acs.joc.2c02030 PubMed ID: 36542602
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Abstract: Chiral cyclopropanols are highly desirable building blocks for medicinal chemistry, but the stereoselective synthesis of these molecules remains challenging. Here, a novel strategy is reported for the diastereo- and enantioselective synthesis of cyclopropanol derivatives via the biocatalytic asymmetric cyclopropanation of vinyl esters with ethyl diazoacetate (EDA). A dehaloperoxidase enzyme from Amphitrite ornata was repurposed to catalyze this challenging cyclopropanation reaction, and its activity and stereoselectivity were optimized via protein engineering. Using this system, a broad range of electron-deficient vinyl esters were efficiently converted to the desired cyclopropanation products with up to 99.5:0.5 diastereomeric and enantiomeric ratios. In addition, the engineered dehaloperoxidase-based biocatalyst is able to catalyze a variety of other abiological carbene transfer reactions, including N?H/S?H carbene insertion with EDA as well as cyclopropanation with diazoacetonitrile, thus adding to the multifunctionality of this enzyme and defining it as a valuable new scaffold for the development of novel carbene transferases.
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CAS No. : | 403-42-9 | MDL No. : | MFCD00000354 |
Formula : | C8H7FO | Boiling Point : | - |
Linear Structure Formula : | CH3C(O)C6H4F | InChI Key : | ZDPAWHACYDRYIW-UHFFFAOYSA-N |
M.W : | 138.14 | Pubchem ID : | 9828 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
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Production Example 1 3-(4-Fluerophenyl)-1H-pyrazole 25 g 4'-fluoroacetophenone and 24 g N,N-dimethylformamide dimethyl acetal were heated for 6 hours under reflux, concentrated and evaporated into dryness to give 34.3 g of a reddish brown solid.. The product was dissolved in 150 ML ethanol, and 9.9 ML hydrazine monohydrate was added thereto and heated at 70C for 2 hours.. The reaction solution was poured into water, extracted with ethyl acetate and dried over magnesium sulfate, and the solvent was evaporated.. The product was recrystallized from ethyl acetate and hexane to give 24.5 g pale yellow crystals.1H-NMR (CDCl3) delta: 6.57(d, J=2. 4Hz, 1H), 7.05-7.12(m, 2H), 7.60(d, J=2. 4Hz, 1H), 7.70-7.76(m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
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With peracetic acid; sulfuric acid; nitric acid; acetic acid; In water; | Example 23 Preparation of 4-fluoro-3-nitrophenol (23) To 15 mL of concentrated sulfuric acid at 0° C. is added 6.9 g (0.05 mmol) of 4-fluoroacetophenone. To the resulting solution is rapidly added a mixture of 4 mL nitric acid and 6 mL concentrated sulfuric acid. The reaction mixture is stirred at 0-5° C. for 3 hours. The reaction mixture is then poured into ice water, and the resulting mixture is extracted with chloroform. The combined organic fractions are washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified using column chromatography on silica gel, eluding with 20percent ethyl acetate/hexanes, yielding 6.0 g of 4-fluoro-3-nitroacetophenone (60percent yield). Concentrated sulfuric acid (200 mL) and acetic acid (120) mL are mixed at 0° C. To this solution is added 15 g (0.082 mol) of 4-fluoro-3-nitroacetophenone with stirring. To the cold reaction mixture is added 36 mL of 36percent peracetic acid. The reaction mixture is then stirred at room temperature for 4 hours. Water (500 mL) is added to the mixture, and the crude product is extracted into diethyl ether. The combined ether fractions are washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified using column chromatography on silica gel, eluding with 3percent methanol/chloroform, giving 3.2 g of Compound 23 (20percent yield). mp: 86-87° C. 1 H-NMR (CDCl3) 7.56 (dd, 1H); 7.29 (t, 1H), 7.12 (m, 1H); 5.36 (s, 1H). 19 F-NMR (d6 -DMSO) 147.60 (s). Anal. calc. for C6 H4 FNO3: C, 45.87; H, 2.57; N, 8.92. Found: C, 45.80; H. 2.51; N, 8.69. |
Yield | Reaction Conditions | Operation in experiment |
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With sodium hydroxide; In ethanol; at 20℃; | General procedure: p-Fluoro acetophenone 6 (0.01 mol) and benzaldehyde Ia(0.01 mol) were dissolved in 15 mL ethanol. NaOH solution(0.02 mol) in ethanol was added slowly and the mixture wasstirred at 20 °C for 2 h until the entire mixture becomes verythick. The progress of the reaction was monitored by TLC(toluene: acetone, 80:20). Then the reaction mixture waspoured slowly onto 400 mL of water with stirring and keptin refrigerator for 24 h. The precipitate obtained was filtered,washed, and recrystallized from ethanol. The othercompounds IIb?j were prepared by the same method usingsubstituted benzaldehydes Ib?j. |
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