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Diethylaluminum Iodide Promoted Morita–Baylis–Hillman Reaction of D ‐Glucose‐Derived Densely O ‐Functionalized Cyclopentenone: Route to α‐C‐Branched Densely Functionalized Cyclic Enones
Author(s) -
Ghosal Partha,
Ajay Sama,
Bajpai Vikas,
Kumar Brijesh,
Shaw Arun K.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200661
Subject(s) - cyclopentenone , chemistry , iodide , methyl iodide , organic chemistry , adduct , baylis–hillman reaction , lewis acids and bases , catalysis
Morita–Baylis–Hillman (MBH) reaction of D ‐glucose‐derived highly O ‐functionalized cyclopentenone is described for the first time. The MBH reaction of cyclopentenone with different aldehydes in the presence of diethylaluminum iodide proceeded smoothly in moderate to good yields. Promoters such as organic, inorganic, or Lewis bases and an aqueous medium are not suitable conditions for the MBH reaction of highly O ‐functionalized cyclopentenones with aldehydes.