Journal
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
Volume 57, Issue 6B, Pages 1237-1242Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/jccs.201000183
Keywords
Allylic oxidation; Allylic acetoxylation; Allylic esterification; Cu allylic oxidation; Cholesterol diacetate
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Funding
- National Natural Science Foundation of China [20876011, 20876012]
- Beijing Natural Foundation [2071002]
- Beijing 973 High-Tech Project [2007CB707804, 2009CB724703]
- Beijing Municipal Science and Technology Commission [Z0901030084091]
- Beijing 863 High-Tech Project [2007AA100404, 2087AA10Z360, 2009AA10Z404, 2009AA02Z207, 2009AA05Z436, 2009AA033001, 2009AA033002]
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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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