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Novel approach to stereoselective synthesis of (E)/(Z)-(N-acyl-oxazolidinone)-eneglycinates

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Abstract

(E)-(N-Acyl-oxazolidinone)-eneglycinates were synthesized with high stereoselectivity and in good yield by condensation of aldehydes with glycinates. (Z)-Eneglycinates could be prepared in high purity and moderate yield by transformation of (E)-eneglycinates under mild conditions. The effect on the (E)/(Z)-configuration of eneglycinates of steric hindrance by α-substituents on the aldehyde was also examined. The software MMFF94 was used to explain the transformation of the thermodynamic product into the kinetic product and a plausible mechanism is given.

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Authors and Affiliations

  1. State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, China

    Qidong You

  2. Jiangsu Key Laboratory of Drug Design and Optimization, Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing, 210009, Jiangsu, China

    Yanyan Zhang & Haopeng Sun

Authors
  1. Yanyan Zhang
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  2. Haopeng Sun
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  3. Qidong You
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Correspondence to Qidong You.

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Zhang, Y., Sun, H. & You, Q. Novel approach to stereoselective synthesis of (E)/(Z)-(N-acyl-oxazolidinone)-eneglycinates. Res Chem Intermed 41, 749–760 (2015). https://doi.org/10.1007/s11164-013-1225-x

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