高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (1): 56.

• 论文 • 上一篇    下一篇

α-取代内酯的立体选择硝基乙烯化反应研究

王锐2, 杨晓武2, 刘大学2, 贾强1   

  1. 1. 兰州大学生物系、化学系, 兰州, 730000;
    2. 应用有机化学国家重点实验室, 兰州, 730000
  • 收稿日期:1997-01-06 出版日期:1998-01-24 发布日期:1998-01-24
  • 通讯作者: 王锐,男,35岁,教授.
  • 作者简介:王锐,男,35岁,教授.
  • 基金资助:

    国家自然科学基金(29442010)、霍英东教育基金、国家教委优秀年轻教师基金和博士点专项科研基金资助课题.

Stereoselective Nitroolefination of α-Substituted Lactones

WANG Rui2, YANG Xiao-Wu2, LIU Da-Xue2, JIA Qiang1   

  1. 1. Department of Biology, Department of Chemistry， Lanzhou, 730000;
    2. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000
  • Received:1997-01-06 Online:1998-01-24 Published:1998-01-24

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摘要： 研究了α-取代内酯的立体选择硝基乙烯化反应.从金属离子对反应时间、温度及产率的影响实验中发现,Zn2+增加了反应活性.用1H NMR光谱确定了产物双键的立体构型,并初步探讨了反应历程.

关键词: &alpha, -硝基乙烯内酯, 季碳中心, 立体选择合成

Abstract: Nitroolefins are versatile intermediates in the synthesis of complex natural products because of their various functional group transformations. They can proceed Michael type additions, and Diels-Alder cyclic reactions. Furthermore, the--NO2 group can be converted to carbonyl group by reductive Nef reaction. Their synthetic potential should be greatly enhanced if they contain quaternary carbon centers. Here, we wish to describe stereoselective nitroolefination of α-substituted carbonyl compounds via addition-elimination on the basis of our previous research. The E stereochemistry of double bond was determined by 1H NMR data (chemical shift, the coupling constant). Studies on effects of different metal ions on reaction temperature, time and yields showed Zn2+ enhanced reactivity. A rational process of addition-elimination was proposed to elucidate the reaction mechanism.

Key words: Nitroolefinic lactone, Quaternary carbon center, Stereoselective synthesis

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