有机化学 ›› 2011, Vol. 31 ›› Issue (06): 908-911. 上一篇    下一篇

研究简报

Boc或Cbz保护的L-脯氨醇衍生物的稳定性

王阁,曹小辉,孙慧超,陈立功*   

  1. (天津大学化工学院 天津 300072)
  • 收稿日期:2010-09-29 修回日期:2010-12-31 发布日期:2011-02-10
  • 通讯作者: 陈立功 E-mail:lgchen@tju.edu.cn

Stability of Cbz or Boc Protected L-Prolinol Derivatives

WANG Ge, CAO Xiao-Hui, SUN Hui-Chao, CHEN Li-Gong   

  1. (School of Chemical Engineering, Tianjin University, Tianjin 300072)
  • Received:2010-09-29 Revised:2010-12-31 Published:2011-02-10
  • Contact: Ligong Chen E-mail:lgchen@tju.edu.cn

近年来, L-脯氨醇衍生物催化的不对称Michael加成反应已经成为手性催化研究领域的热点. 而在L-脯氨醇衍生物的合成中, 常常涉及到L-脯氨醇氨基的保护. 为此, 研究了Boc和Cbz保护的脯氨醇衍生物的稳定性, 发现Boc保护的L-脯氨醇在羟基被取代为易离去基团时, 就变得不稳定, 在67 ℃就发生分子内环合生成化合物γ-丁内酯|而Cbz保护的L-脯氨醇衍生物的稳定性要好得多, 在140 ℃且有三乙胺存在时, 才会发生类似的分子内环合反应.

关键词: 脯氨醇衍生物, 稳定性, Cbz保护, Boc保护, 环合

Recently, the asymmetric Michael addition mediated by the derivatives of L-prolinol has been a big hit in the field of asymmetric synthesis. However, the protection of the amino group of L-prolinol is a key step and often involved in the synthesis of L-prolinol derivatives. Thus, the stability of Cbz or Boc protected L-prolinol derivatives is investigated. It was found that when the hydroxyl group of Boc protected L-prolinol is replaced by easily leaving group, it is unstable and cyclization proceeds effectively to give γ-butyrolactone at 67 ℃|however, Cbz protected L-prolinol derivatives are more stable, similar cyclization will happen at 140 ℃ in the presence of triethylamine.

Key words: derivative of prolinol, stability, Cbz protection, Boc protection, cyclization