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Direct Cu‐Catalyzed Allylic Acetoxylation of Δ 5 ‐Steroids at 7‐Position
Author(s) -
Rahman Faiz Ur,
Rahman Ata Ur,
Tan TianWei
Publication year - 2010
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201000183
Subject(s) - allylic rearrangement , chemistry , yield (engineering) , catalysis , selectivity , solvent , alkene , metal , organic chemistry , medicinal chemistry , metallurgy , materials science
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 Δ 5 ‐steroids at 7‐position, for which the resulting acetoxylated product obtained was exclusively α‐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.