Pseudocine substitution of 4-(mesyloxy)-2-cyclopentenones: an efficient route to 2,4-disubstituted 2-cyclopentenones

West, F. G.; Gunawardena, G. U.

doi:10.1021/jo00061a010

Cited by 25 publications

(10 citation statements)

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“…The organic extracts were combined and solvent was evaporated. The residue was purified by column chromatography on silica gel (10 g, hexane:AcOEt, 6:4) to give (±)‐ 4b containing ~1% of 5b (406 mg, 42% yield): 1 H NMR (400 MHz) 7.51 (dd, J = 5.6, 2.4 Hz, 1H), 6.16 (dd, J = 5.6, 1.2 Hz, 1H), 4.80‐4.79 (m, 1H), 2.39 (brs, 1H, OH), 2.32‐2.24 (m, 1H), 2.19 (dd, J = 4.4, 2.4 Hz, 1H), 1.09 (d, J = 6.8 Hz, 3H), 0.83 (d, J = 6.8 Hz, 3H); 13 C NMR (100 MHz): 208.2, 162.2, 134.9, 72.8, 60.8, 27.1, 20.7 and 20.2, in agreement with reported data …”

Section: Methodsmentioning

confidence: 99%

“…The organic extracts were combined and solvent was evaporated. The residue was purified by column chromatography on silica gel (10 g, hexane:AcOEt, 6:4) to give (±)-4b containing~1% of 5b (406 mg, 42% yield): 7,21,22 An analogous experiment carried out over an extended reaction time afforded (±)-4b contaminated with a side product to which the structure of (±)-5b was tentatively assigned, 1 The stirred mixture was cooled to -78°C and n-butyllithium (2.32 M in hexane, 54 mL, 0.13 mol; 1 equiv) was added dropwise maintaining the temperature below -65°C. After completed addition, the mixture was allowed to warm to 0°C (a white cloudy precipitate appeared).…”

Section: -Furyl Isopropyl Carbinol [(±)-3b]mentioning

confidence: 99%

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Chemoenzymatic Approach to Optically Active 4‐Hydroxy‐5‐alkylcyclopent‐2‐en‐1‐one Derivatives: An Application of a Combined Circular Dichroism Spectroscopy and DFT Calculations to Assignment of Absolute Configuration

et al. 2014

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A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated electronic circular dichroism [ECD] and vibrational circular dichroism [VCD] spectra) to determine the absolute configuration of both stereogenic centers in 4-hydroxy-5-methylcyclopent-2-en-1-one was demonstrated. It was also demonstrated that the concurrent application of ECD and VCD spectroscopy can be used for the determination of the configuration of two stereogenic centers.

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Section: Methodsmentioning

confidence: 99%

Section: -Furyl Isopropyl Carbinol [(±)-3b]mentioning

confidence: 99%

Chemoenzymatic Approach to Optically Active 4‐Hydroxy‐5‐alkylcyclopent‐2‐en‐1‐one Derivatives: An Application of a Combined Circular Dichroism Spectroscopy and DFT Calculations to Assignment of Absolute Configuration

et al. 2014

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“…The literature survey showed that 14 was significantly more stable than common β‐acetoxy ketone and resistant to β‐elimination . Hypothetically, 4‐acetoxy cyclopentenone ( 14 ) could be used for cysteine protein modification through the mechanism of Michael addition ( 15 a ) with rapid elimination ( 15 b ) that is similar to reported small molecule reactions . β‐Elimination could occur rapidly on 15 a only after Michael addition due to the unfavored antiaromatic nature of 16, which would provide selectivity for cysteine.…”

Section: Methodsmentioning

confidence: 99%

Highly Reactive and Tracelessly Cleavable Cysteine‐Specific Modification of Proteins via 4‐Substituted Cyclopentenone

Yang

Sun

et al. 2018

Angew Chem Int Ed

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A rapid and cysteine-specific modification of proteins using 4-substituted cyclopentenone via a Michael addition tandem elimination reaction was developed. Compared to the classical method, this reaction featured fast kinetics with a stable product. More importantly, this conjugation could be tracelessly removed by exchange with a Michael addition donor. The conjugation and regeneration process not only exhibited little change to the structures or conformations of the proteins but also exhibited little disturbance to their biological functions, such as their enzymatic activities.

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“…[10f] 4b, [23] 5b, [24] 6b, [25] 7b [26] ). Baker×s yeast was employed as obtained from the Hofer and AstrˆCo.…”

Section: Methodsmentioning

confidence: 99%

Simple Biocatalytic Access to Enantiopure (S)‐1‐Heteroarylethanols Employing a Microbial Hydrogen Transfer Reaction

et al. 2004

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Lyophilised cells of various Rhodococcus spp. were employed in an efficient hydrogen transferlike process for the asymmetric bioreduction of heteroaryl methyl ketones using 2-propanol as hydrogen donor. Besides the genus Rhodococcus, only Mycoplana rubra R14 showed a comparable stability towards elevated concentrations of the co-substrate 2-propanol. Among the organisms tested, Rhodococcus ruber DSM 44541 and DSM 43338 showed best activity and selectivity. With these strains, the reaction proceeded with high stereoselectivity (ee >99%) and predictable stereochemical outcome regardless of the nature of the heteroaromatic ring system. The reaction could be performed at the exceptional substrate concentration of up to 0.4 mol L À1 in an environmentally friendly aqueous-organic solvent mixture at room temperature and is easy to handle, thus providing a very practical tool to access enantiopure 1-heteroarylethanols.

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Pseudocine substitution of 4-(mesyloxy)-2-cyclopentenones: an efficient route to 2,4-disubstituted 2-cyclopentenones

Cited by 25 publications

References 0 publications

Chemoenzymatic Approach to Optically Active 4‐Hydroxy‐5‐alkylcyclopent‐2‐en‐1‐one Derivatives: An Application of a Combined Circular Dichroism Spectroscopy and DFT Calculations to Assignment of Absolute Configuration

Chemoenzymatic Approach to Optically Active 4‐Hydroxy‐5‐alkylcyclopent‐2‐en‐1‐one Derivatives: An Application of a Combined Circular Dichroism Spectroscopy and DFT Calculations to Assignment of Absolute Configuration

Highly Reactive and Tracelessly Cleavable Cysteine‐Specific Modification of Proteins via 4‐Substituted Cyclopentenone

Simple Biocatalytic Access to Enantiopure (S)‐1‐Heteroarylethanols Employing a Microbial Hydrogen Transfer Reaction

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