82290-03-7Relevant academic research and scientific papers
DIRECTED METALLATIONS OF 4-ETHYLIDENETERONIC ACID AND ITS DERIVATIVES AS A SYNTHETIC ENTRY TO NATURAL 4-OXY-2-FURANONES
Clemo, Nicholas G.,Pattenden, Gerald
, p. 581 - 584 (1982)
Lithium diisoprpylamide (LDA) removes the α-proton from the O-methyl tetronic acid (2b) leading to the vinylic carbanion (12), whereas treatment of the trimethylsilyl derivative (14) with LDA, followed by reaction with aldehydes gives products resulting from both γ- and ε-addition; the directed metallations provide access to a range of 4-oxy-2-furanone derivatives found amongst natural products.
Directed Metallations of 4-Ethylidenetetronic Acid O-Methyl Ether and its Derivatives as a Synthetic Entry to Natural 4-Oxyfuran-2-ones
Buck, Judith,Clemo, Nicholas G.,Pattenden, Gerald
, p. 2399 - 2406 (2007/10/02)
Lithium di-isopropylamide removes the C-2(α-)-protons from the O-methyl tetronates (11) and (20) in a regioselective manner leading to the corresponding novel anions e.g. (18).The vinyl anions then react with a range of electrophiles providing a preparati
