7623-10-1Relevant articles and documents
Cu(I)-catalyzed oxidative cyclization of alkynyl oxiranes and oxetanes
Gronnier, Colombe,Kramer, Soren,Odabachian, Yann,Gagosz, Fabien
supporting information; experimental part, p. 828 - 831 (2012/03/07)
In the presence of a Cu(I) catalyst and a pyridine oxide, alkynyl oxiranes and oxetanes can be converted into functionalized five- or six-membered α,β-unsaturated lactones or dihydrofuranaldehydes. This new oxidative cyclization is proposed to proceed via an unusual allenyloxypyridinium intermediate.
An improved synthesis of captopril
Nam,Lee,Ryu
, p. 1843 - 1844 (2007/10/02)
An improved synthesis of captopril using methacrylic acid as the starting material is described. Treatment of methacrylic acid (I) with a hydrogen halide gave the 3-halogeno-2-methylpropanoic acids II and III, which were treated with thionyl chloride to yield the corresponding 3-halogeno-2-methylpropanoyl chlorides IV and V. Treatment of IV or V with L-proline yielded the N-(R,S-3-halogeno-2-methylpropanoyl)-L-prolines VI and VII, which were separated into optically pure R- and S-diastereoisomers using dicyclohexylamine. Treatment of halides of VI or VII with methanolic ammonium hydrosulfide gave captopril in 28% yield.