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Staudinger synthesis : ウィキペディア英語版 | Staudinger synthesis
The Staudinger Synthesis, also called the Staudinger Ketene-Imine Cycloaddition, is a chemical synthesis in which an imine reacts with a ketene through a non-photochemical 2+2 cycloaddition to produce a ''β''-lactam. The reaction carries particular importance in the synthesis of β-Lactam antibiotics. The Staudinger Synthesis should not be confused with the Staudinger Reaction, a phosphine or phosphite reaction used to reduce azides to amines. Reviews on the mechanism, stereochemistry, and applications of the reaction have been published.〔Fu, N.; Tidwell, T. T. "Preparation of β-lactams by () cycloaddition of ketenes and imines" ''Tetrahedron'' 2008, ''64'', 10465-10496. (())〕 ==History== The reaction was discovered in 1907 by the German chemist Hermann Staudinger. The reaction did not attract interest until the 1940s, when the structure of penicillin was elucidated. The ''β''-lactam moiety of the first synthetic penicillin was constructed using this cycloaddition, and it remains a valuable tool in synthetic organic chemistry.
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