SIOC English
有机化学
高级检索

有机化学 ›› 1993, Vol. 13 ›› Issue (3): 244-249. 上一篇    下一篇

研究论文

光学活性姜黄烯化合物的立体选择性合成

王智贤;陈钟瑛   

  1. 华东化工学院化学制药研究室
  • 发布日期:1993-06-25

Stereoselective synthesis of optically active curcumenes

WANG ZHIXIAN;CHEN ZHONGYING   

  • Published:1993-06-25

被引次数

1

本文报道了在手性膦过渡金属配合物催化下,以对溴甲苯与6-甲基-5-庚烯-2-溴化镁(5)经不对称交叉偶联反应合成(R)-(-)-和(S)-(+_)-α-姜黄烯的方法,光学收率分别为44%e.e和50.3%e.e.(R)-(-)-α-姜黄烯经Birch还原得到(R)-(-)-β-姜黄烯.对溴苯甲醚经不对称交叉偶联、Birch还原等反应合成了(S)-(+)-γ-姜黄烯.

关键词: 庚烯 P, 倍半萜, 过渡金属络合物, 催化剂, 格氏试剂, 苯 P, 膦, 手征性, 精油, 溴代烃

A new and feasible method for synthesizing optically active (R)- and (S)-(+)-a-curcumene (I) via 6-methyl-5-hepten-2-ylmagnesium bromide asym. cross-coupling reaction with p-bromotoluene catalyzed by chiral phosphine-transition metal complexes, in optical yield up to 50% e.e., was described. (R)-(-)-a-Curcumene was converted into (R)-(-)-b-curcumene (II) by Birch reduction (S)-(+)-g-Curcumene (III) was synthesized from p-bromophenylmethyl ether via asym. cross-coupling, Birch reduction etc.

Key words: CATALYST, HEPTENE P, GRIGNARD REAGENT, TRANSITION METAL COMPLEX, BENZENE P, SESQUITERPENE, ESSENCIAL OIL, PHOSPHINE, BROMOHYDROCARBON, CHIRALITY

中图分类号: