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Thermally Induced and Silver-Salt-Catalyzed [2+2] Cycloadditions of Imines to (Alkoxymethylene)cyclopropanes

Itaru Nakamura*, Tetsuya Nemoto, Yoshinori Yamamoto, Armin de Meijere

*Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Email:

T. Nishimura, Y. Yasuhara, T. Hayashi, Angew. Chem. Int. Ed., 2006, 45, 5164-5166.

DOI: 10.1002/anie.200600961 (free Supporting Information)

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Thermal and silver-catalyzed [2+2] cycloadditions of imines to methylenecyclopropane derivatives gave 2-alkoxyazetidines, which are versatile building blocks for the synthesis of various other compounds such as α-cyclopropanated β-amino acids.

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Key Words

azetidines, amino acids, cycloaddition, cyclopropanes, homogeneous catalysis, silver

ID: J06-Y2006-2430