The first samarium(II)-mediated stereoselective spirocyclization onto an aromatic ring.

Chem Commun (Camb)

Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.

Published: February 2002

The first samarium(II)-mediated spirocyclisation onto an aromatic ring was achieved by the reaction of methyl 4-(4-oxoalkyl)benzoates with SmI2 in the presence of i-PrOH and HMPA, yielding methyl 1-alkyl-1-hydroxyspiro-[4.5]dec-6-ene-8-carboxylates in moderate to high yields.

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http://dx.doi.org/10.1039/b110633cDOI Listing

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