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The Enders SAMP/RAMP hydrazone alkylation reaction is an asymmetric carbon-carbon bond formation reaction facilitated by pyrrolidine chiral auxiliaries. It was pioneered by E. J. Corey and D. Enders in 1976, and was further developed by D. Enders and his group. This method is usually a three-step sequence. The first step is to form the hydrazone between (S)-1-amino-2-methoxymethylpyrrolidine (SAMP) or (R)-1-amino-2-methoxymethylpyrrolidine (RAMP) and a ketone or aldehyde. Afterwards, the hydrazone is deprotonated by lithium diisopropylamide (LDA) to form an azaenolate, which reacts with alkyl halides or other suitable electrophiles to give alkylated hydrazone species with the simultaneous generation of a new chiral center. Finally, the alkylated ketone or aldehyde can be regenerated by ozo

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  • The Enders SAMP/RAMP hydrazone alkylation reaction is an asymmetric carbon-carbon bond formation reaction facilitated by pyrrolidine chiral auxiliaries. It was pioneered by E. J. Corey and D. Enders in 1976, and was further developed by D. Enders and his group. This method is usually a three-step sequence. The first step is to form the hydrazone between (S)-1-amino-2-methoxymethylpyrrolidine (SAMP) or (R)-1-amino-2-methoxymethylpyrrolidine (RAMP) and a ketone or aldehyde. Afterwards, the hydrazone is deprotonated by lithium diisopropylamide (LDA) to form an azaenolate, which reacts with alkyl halides or other suitable electrophiles to give alkylated hydrazone species with the simultaneous generation of a new chiral center. Finally, the alkylated ketone or aldehyde can be regenerated by ozonolysis or hydrolysis. This reaction is a useful technique for asymmetric α-alkylation of ketones and aldehydes, which are common synthetic intermediates for medicinally interesting natural products and other related organic compounds. These natural products include (-)-C10-demethyl arteannuin B, the structural analog of antimalarial artemisinin, the polypropionate metabolite (-)-denticulatin A and B isolated from , zaragozic acid A, a potent inhibitor of sterol synthesis, and epothilone A and B, which have been proven to be very effective anticancer drugs. (en)
  • La reacción de alquilación de hidrazona SAMP / RAMP de Enders es una reacción asimétrica de formación de enlaces carbono-carbono facilitada por auxiliares quirales de pirrolidina. Fue iniciado por E. J. Corey y D. Enders en 1976.​​ Este método suele ser una secuencia de tres pasos. El primer paso es formar la hidrazona entre (S) -1-amino-2-metoximetilpirrolidina (SAMP) o (R) -1-amino-2-metoximetilpirrolidina (RAMP) y una cetona o aldehído. Posteriormente, la hidrazona se desprotona con diisopropilamida de litio (LDA) para formar un azaenolato, que reacciona con haluros de alquilo u otros electrófilos adecuados para dar especies de hidrazona alquilada con la generación simultánea de un nuevo centro quiral. Finalmente, la cetona o aldehído alquilado se puede regenerar por ozonólisis o hidrólisis.​ Esta reacción es una técnica útil para la α-alquilación asimétrica de cetonas y aldehídos, que son intermedios sintéticos comunes para productos naturales de interés medicinal y otros compuestos orgánicos relacionados. Estos productos naturales incluyen (-) - C10-desmetil arteannuína B, el análogo estructural de la artemisinina antipalúdica, el metabolito tipo polipropionato (-) - A y B aislados de , ácido zaragózico A, un potente inhibidor de la síntesis de esteroles, y A y B, que han demostrado ser medicamentos contra el cáncer muy eficaces.​​​​ (es)
  • SAMP/RAMP-алкилирование — методология стереоселективного синтеза, предложенная Э. Кори и в 1976 году. Данный подход предназначен для направленного алкилирования карбонильных соединений по α-положению. Он основан на использовании хиральных гидразинов SAMP и RAMP — производных (S)- и (R)-пролина соответственно — в качестве . (ru)
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  • SAMP/RAMP-алкилирование — методология стереоселективного синтеза, предложенная Э. Кори и в 1976 году. Данный подход предназначен для направленного алкилирования карбонильных соединений по α-положению. Он основан на использовании хиральных гидразинов SAMP и RAMP — производных (S)- и (R)-пролина соответственно — в качестве . (ru)
  • The Enders SAMP/RAMP hydrazone alkylation reaction is an asymmetric carbon-carbon bond formation reaction facilitated by pyrrolidine chiral auxiliaries. It was pioneered by E. J. Corey and D. Enders in 1976, and was further developed by D. Enders and his group. This method is usually a three-step sequence. The first step is to form the hydrazone between (S)-1-amino-2-methoxymethylpyrrolidine (SAMP) or (R)-1-amino-2-methoxymethylpyrrolidine (RAMP) and a ketone or aldehyde. Afterwards, the hydrazone is deprotonated by lithium diisopropylamide (LDA) to form an azaenolate, which reacts with alkyl halides or other suitable electrophiles to give alkylated hydrazone species with the simultaneous generation of a new chiral center. Finally, the alkylated ketone or aldehyde can be regenerated by ozo (en)
  • La reacción de alquilación de hidrazona SAMP / RAMP de Enders es una reacción asimétrica de formación de enlaces carbono-carbono facilitada por auxiliares quirales de pirrolidina. Fue iniciado por E. J. Corey y D. Enders en 1976.​​ Este método suele ser una secuencia de tres pasos. El primer paso es formar la hidrazona entre (S) -1-amino-2-metoximetilpirrolidina (SAMP) o (R) -1-amino-2-metoximetilpirrolidina (RAMP) y una cetona o aldehído. Posteriormente, la hidrazona se desprotona con diisopropilamida de litio (LDA) para formar un azaenolato, que reacciona con haluros de alquilo u otros electrófilos adecuados para dar especies de hidrazona alquilada con la generación simultánea de un nuevo centro quiral. Finalmente, la cetona o aldehído alquilado se puede regenerar por ozonólisis o hidról (es)
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  • Alquilación de Enders SAMP/RAMP de hidrazonas (es)
  • Enders SAMP/RAMP hydrazone-alkylation reaction (en)
  • SAMP/RAMP-алкилирование (ru)
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