Novel approach to stereoselective synthesis of (E)/(Z)-(N-acyl-oxazolidinone)-eneglycinates
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- 作者：Yanyan Zhang ; Haopeng Sun ; Qidong You
- 关键词：Eneglycinates ; Stereoselectivity ; Steric hindrance ; Configuration
- 刊名：Research on Chemical Intermediates
- 出版年：2015
- 出版时间：February 2015
- 年：2015
- 卷：41
- 期：2
- 页码：749-760
- 全文大小：836 KB
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- 刊物主题：Chemistry
Catalysis
Physical Chemistry
Inorganic Chemistry - 出版者：Springer Netherlands
- ISSN：1568-5675
文摘
(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.