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

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

A silver lining: [2+2] Cycloadditions of imines 2 to (alkoxymethylene)cyclopropanes 1 proceed readily at 80 °C and ambient pressure to furnish spirocyclopropanated 2‐alkoxyazetidines 3 in good to excellent yields. The same reaction can be brought about at 30 °C in the presence of a catalytic amount...

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Veröffentlicht in:Angewandte Chemie International Edition 2006-08, Vol.45 (31), p.5176-5179
Hauptverfasser: Nakamura, Itaru, Nemoto, Tetsuya, Yamamoto, Yoshinori, de Meijere, Armin
Format: Artikel
Sprache:eng
Schlagworte:
amino acids
cycloaddition
cyclopropanes
homogeneous catalysis
silver
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Zusammenfassung:A silver lining: [2+2] Cycloadditions of imines 2 to (alkoxymethylene)cyclopropanes 1 proceed readily at 80 °C and ambient pressure to furnish spirocyclopropanated 2‐alkoxyazetidines 3 in good to excellent yields. The same reaction can be brought about at 30 °C in the presence of a catalytic amount of [Ag(fod)] (fod=6,6,7,7,8,8,8‐heptafluoro‐2,2‐dimethyl‐3,5‐octanedionato).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200600961