Chinese Journal of Organic Chemistry >
Asymmetric Synthesis of β-Amino Phosphonate Derivatives throughNatural Amino Acids Derived α-Diazophosphonates
Received date: 2015-04-23
Revised date: 2015-06-02
Online published: 2015-06-12
Supported by
Project supported by the Committee of Science and Technology of Tianjin City (No. 15JCYBJC20700) and the Xinjiang Laboratory of Native Medicinal and Edible Plant Resources Chemistry Open Subject (2015KL030).
An efficient procedure was developed for the asymmetric synthesis of (S)-diethyl (2-(1,3-dioxoisoindolin-2-yl)propyl)phosphonates employing (S)-diethyl (1-diazo-2-(1,3-dioxoisoindolin-2-yl)alkyl)phosphonates as starting materials. The reaction was catalyzed by 5% Pd/C and used glacial acetic acid as additive in i-PrOH as solvent. The obtained optical β-amino phosphonate derivatives were identified by 1H NMR, 13C NMR, 31P NMR and HRMS and the enantiomeric excess was 95%. This process provided straightforward access to optical β-aminophosphonate derivatives in good yields with high stereoselectivities.
Hu Chenfei , Cai Yan , Munira· , Abudukeremu , Miao Zhiwei . Asymmetric Synthesis of β-Amino Phosphonate Derivatives throughNatural Amino Acids Derived α-Diazophosphonates[J]. Chinese Journal of Organic Chemistry, 2015 , 35(10) : 2135 -2141 . DOI: 10.6023/cjoc201504035
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