Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1657-1664.DOI: 10.6023/cjoc201504021 Previous Articles     Next Articles

ARTICLE

氯霉素衍生噁唑烷酮的合成及其在Aldol反应中的不对称诱导作用

李薇, 李云峰, 俞晓明   

  1. 中国医学科学院药物研究所 天然药物活性物质与功能国家重点实验室 北京 100050
  • 收稿日期:2015-04-14 修回日期:2015-04-27 发布日期:2015-05-06
  • 通讯作者: 俞晓明 E-mail:mingxyu@imm.ac.cn
  • 基金资助:

    国家自然科学基金(No. 21272279)资助项目.

Synthesis of Oxazolidinone Derivative from Chloramphenicol and Its Asymmetric Induction in Aldol Reaction

Li Wei, Li Yunfeng, Yu Xiaoming   

  1. State Key Laboratory of Bioactive Substance and Function of Nature Medicine, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050
  • Received:2015-04-14 Revised:2015-04-27 Published:2015-05-06
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272279).

A new oxazolidinone chiral auxiliary was prepared from chloramphenicol in 5 steps. Aldol reactions between enolates bearing this auxiliary and varied aldehydes in the presence of TiCl4/N,N'-tetramethylethalenediamine (TMEDA) were found to proceed in high yield (>80%) and diastereoselectivity (dr≥19:1) to give Evans syn-aldol adducts.

Key words: chloramphenicol, oxazolidinone chiral auxiliary, asymmetric aldol reaction