A novel samarium(II)-mediated tandem spirocyclization onto an aromatic ring

A novel samarium(II)-mediated tandem spirocyclization onto an aromatic ring

We report a samarium(II)-mediated tandem spirocyclization reaction to provide dispiro[4.2.4.2]tetradecadiene and dispiro[4.2.5.2]pentadecadiene skeletons. The reaction was achieved by intramolecular addition of a ketyl radical onto an aromatic ring bearing an electrophilic moiety followed by reducti...

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Veröffentlicht in:Tetrahedron letters 2011-04, Vol.52 (15), p.1770-1772
Hauptverfasser: Iwasaki, Hiroki, Tsutsui, Nozomi, Eguchi, Toru, Ohno, Hiroaki, Yamashita, Masayuki, Tanaka, Tetsuaki
Format: Artikel
Sprache:eng
Schlagworte:
Aromatic compounds
Bearing
Radicals
Tetrahedrons
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Zusammenfassung:We report a samarium(II)-mediated tandem spirocyclization reaction to provide dispiro[4.2.4.2]tetradecadiene and dispiro[4.2.5.2]pentadecadiene skeletons. The reaction was achieved by intramolecular addition of a ketyl radical onto an aromatic ring bearing an electrophilic moiety followed by reductive capture of the spirohexadienyl radical intermediate with SmI sub(2 in the presence of HMPA.)
ISSN:0040-4039
DOI:10.1016/j.tetlet.2011.02.010