75116-78-8Relevant academic research and scientific papers
Synthesis of the precursor of anti-inflammatory agents by cross-coupling using electrogenerated highly reactive zinc
Jalil, Aishah A.,Kurono, Nobuhito,Tokuda, Masao
, p. 2681 - 2686 (2002)
Highly reactive zinc metal was readily prepared by electrolysis of a DMF solution containing naphthalene and a supporting electrolyte in a one-compartment cell fitted with a platinum cathode and a zinc anode. This reactive zinc was used for efficient transformation of ethyl 2-bromoacrylate into the corresponding organozinc compound, which was reacted with various aryl iodides in the presence of palladium catalyst to give the corresponding cross-coupling products, ethyl 2-arylpropenoates, in high yields. These cross-coupling reactions were successfully applied to a synthesis of the precursors of non-steroidal anti-inflammatory agents such as ibuprofen, naproxen, ketoprofen, loxoprofen, indoprofen, suprofen, cicloprofen, and flurbiprofen.
ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE CONFIGURATION OF (+)-α-(3-BENZOYLPHENYL)PROPIONIC ACID
Comisso, Giovanni,Mihalic, Mladen,Kajfez, Franjo,Sunjic, Vitomir,Snatzke, Guenther
, p. 123 - 128 (2007/10/02)
Asymmetric homogeneous hydrogenation of α-(3-benzoylphenyl)acrylic acid (4), which is preparared in 90percent overall yield from (3-benzoylphenyl)acetic acid (1), affords (+)-α-(3-benzoylphenyl)propionic acid, (+)-5, in 93.7percent chemical and 67.4percent optical yield.The absolute configuration of (+)-5 is correlated with that of (+)-(S)-hydratropic acid via (+)-α-(3-benzylphenyl)propionic acid, (+)-6.The origin of the CD bands of (+)-6 is discussed and comparison of chiroptical data with those of (+)-(S)-hydratropic acid, reveals that (+)-6 has an S configuration.Since (+)-6 is chemically correlated with (+)-5, the absolute S configuration of this enantiomer is confirmed.
