高等学校化学学报

高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (S1): 429.

• Synthetic Sciences • 上一篇    下一篇

The Asymmteric Syntheses of Alkaloids via Electro-Oxidation of Aza-Rings

HU Yen-Yi, RU Wan-Huey, WEI Chao-Jen, LIN Sheu-Jen, LAY Yen-Yuan, YEH Shun-Tsai, YANGTeng-Kuei   

  1. Department of Chemistry, National Chung-Hsing University, Taichung
  • 出版日期:2000-12-31 发布日期:2000-12-31

The Asymmteric Syntheses of Alkaloids via Electro-Oxidation of Aza-Rings

HU Yen-Yi, RU Wan-Huey, WEI Chao-Jen, LIN Sheu-Jen, LAY Yen-Yuan, YEH Shun-Tsai, YANGTeng-Kuei   

  1. Department of Chemistry, National Chung-Hsing University, Taichung
  • Online:2000-12-31 Published:2000-12-31

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摘要：

Recently, we found the N-(hydroxyalkyl) aza-rings 1 can produce 2-oxazolidine 2 through electrolysis. With the chiral side chain, the 2-oxazolidine 2 can generate a new chiral center at the 0-aminocarbon when treated with Grignard reagents. Repeat the process of electro-oxidation and substitution by Grignard reagents, we can prepare the two most popular alkaloids bases, pyrroliding and piperidine, with substitutions in an enantioselective fashion. This presentation will discuss the efficiency of electro-oxidation of aza-ring compounds in terms of the oxidation conditions, such as the applied potential, quantity of electricity, solvent effect,and temperature effect. Meanwhile, several demonstrative syntheses of chiral alkaloids, such as Monomorine,(-)-pyrroliding 197B, and(-)-Solenopsin A, will also be presented.

Abstract:

Recently, we found the N-(hydroxyalkyl) aza-rings 1 can produce 2-oxazolidine 2 through electrolysis. With the chiral side chain, the 2-oxazolidine 2 can generate a new chiral center at the 0-aminocarbon when treated with Grignard reagents. Repeat the process of electro-oxidation and substitution by Grignard reagents, we can prepare the two most popular alkaloids bases, pyrroliding and piperidine, with substitutions in an enantioselective fashion. This presentation will discuss the efficiency of electro-oxidation of aza-ring compounds in terms of the oxidation conditions, such as the applied potential, quantity of electricity, solvent effect,and temperature effect. Meanwhile, several demonstrative syntheses of chiral alkaloids, such as Monomorine,(-)-pyrroliding 197B, and(-)-Solenopsin A, will also be presented.

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