有机化学 ›› 2015, Vol. 35 ›› Issue (8): 1657-1664.DOI: 10.6023/cjoc201504021 上一篇    下一篇

研究论文

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 出版日期:2015-08-25 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 Online:2015-08-25 Published:2015-05-06
  • Supported by:

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

以氯霉素为原料, 经五步反应合成了一种新的噁唑烷酮手性辅基, 考察了其在不对称aldol反应中的手性诱导作用. 在TiCl4/N,N'-四甲基乙二胺(TMEDA)存在下, 带有该辅基的酰亚胺烯醇供体可与芳香醛、脂肪醛和α,β-不饱和醛等多种醛顺利反应, 以较高的产率(>80%)和非对映选择性(dr≥19:1)生成Evans型syn-aldol反应产物.

关键词: 氯霉素, 噁唑烷酮手性辅基, 不对称Aldol反应

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