4.3 Article

Direct Cu-Catalyzed Allylic Acetoxylation of Δ5-Steroids at 7-Position

期刊

JOURNAL OF THE CHINESE CHEMICAL SOCIETY
卷 57, 期 6B, 页码 1237-1242

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/jccs.201000183

关键词

Allylic oxidation; Allylic acetoxylation; Allylic esterification; Cu allylic oxidation; Cholesterol diacetate

资金

  1. National Natural Science Foundation of China [20876011, 20876012]
  2. Beijing Natural Foundation [2071002]
  3. Beijing 973 High-Tech Project [2007CB707804, 2009CB724703]
  4. Beijing Municipal Science and Technology Commission [Z0901030084091]
  5. Beijing 863 High-Tech Project [2007AA100404, 2087AA10Z360, 2009AA10Z404, 2009AA02Z207, 2009AA05Z436, 2009AA033001, 2009AA033002]

向作者/读者索取更多资源

The efficiency and selectivity of Cu-catalyzed allylic acetoxylation of alkene in different solvent systems is improved by the presence of different metallic salts in the reaction medium. The methodology is particularly well employed for the direct allylic acetoxylation of Delta(5)-steroids at 7-position, for which the resulting acetoxylated product obtained was exclusively alpha-isomer. Excellent yield was achieved (up to 90%) under optimized conditions, while significantly reducing the costs and environmental hazards and increasing the yield as compared to the other previously reported methods.

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