Darzens Reaction of Acyl Phosphonates with α-Bromo Ketones: Selective Synthesis of <i>cis</i>- and <i>trans</i>-Epoxyphosphonates

Demir, Ayhan S.; Emrullahoğlu, Mustafa; Pirkin, Eser; Akca, Nazmiye

doi:10.1021/jo801818p

Cited by 27 publications

(2 citation statements)

References 44 publications

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“…115 The Darzens condensation of acyl phosphonates 223 with a-halo ketones 224 in the presence of base at room temperature affords cis-and trans-epoxyphosphonates 225 in good chemical yield (Scheme 63). 116 The diastereoselectivity of this condensation reaction is easily controlled by changing the base. When DBU is used, the diastereomeric ratio (trans/cis) reaches up to 8/1.…”

Section: Synthetic Applicationsmentioning

confidence: 99%

2.14 Other Condensation Reactions (Knoevenagel, Perkin, Darzens)

Ebitani

2014

Comprehensive Organic Synthesis II

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Section: Synthetic Applicationsmentioning

confidence: 99%

2.14 Other Condensation Reactions (Knoevenagel, Perkin, Darzens)

Ebitani

2014

Comprehensive Organic Synthesis II

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“…miltiorrhiza, as well as dissatisfactory yield and purity of DSS, limit the natural plant extraction of DSS to meet industrial requirement . Therefore, chemical synthesis routes with classical Knoevenagel condensation and Darzens condensation gradually advance as alternative methods for DSS production. Although chemical synthesis approaches ease the limitation of S.…”

Section: Introductionmentioning

confidence: 99%

Self-Sufficient In Vitro Multi-Enzyme Cascade for Efficient Synthesis of Danshensu froml-DOPA

et al. 2022

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Danshensu (DSS), a traditional Chinese medicine, is widely used for the treatment of cardiovascular and cancer diseases. Here, a one-pot multi-enzyme cascade pathway was designed for DSS synthesis from l-DOPA using tyrosine aminotransferase from Escherichia coli (EcTyrB) and d-isomer-specific 2-hydroxyacid dehydrogenase from Lactobacillus frumenti (LfD2-HDH). Glutamate dehydrogenase from Clostridium difficile (CdgluD) was also introduced for a self-sufficient system of α-ketoglutaric acid and NADH. Under optimal conditions (35 °C, pH 7.0, EcTyrB:LfD2-HDH:CdgluD = 3:2:1, glutamate:NAD+ = 1:1), 98.3% yield (at 20 mM l-DOPA) and space-time yield of 6.61 g L–1 h–1 (at 40 mM l-DOPA) were achieved. Decreased yields of DSS at elevated l-DOPA concentrations (100 mM) could be attributed to an inhibited CdgluD activity caused by NH4 + accumulation. This developed multi-enzyme cascade pathway (including EcTyrB, LfD2-HDH, and CdgluD) provides an efficient and sustainable approach for the production of DSS from l-DOPA.

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Synthesis of Oxiranes and Aziridines from Aldehydes and Imines Using Anionic Homologation Approaches

Delost

Njardarson

2023

Homologation Reactions

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Darzens Reaction of Acyl Phosphonates with α-Bromo Ketones: Selective Synthesis of cis- and trans-Epoxyphosphonates

Cited by 27 publications

References 44 publications

2.14 Other Condensation Reactions (Knoevenagel, Perkin, Darzens)

2.14 Other Condensation Reactions (Knoevenagel, Perkin, Darzens)

Self-Sufficient In Vitro Multi-Enzyme Cascade for Efficient Synthesis of Danshensu froml-DOPA

Synthesis of Oxiranes and Aziridines from Aldehydes and Imines Using Anionic Homologation Approaches

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