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

Author:
Ohno, Hiroaki, Maeda, Shin-ichiro, Okumura, Mitsuaki, Wakayama, Ryutaro, Tanaka, Tetsuaki
Source:
Chemical communications 2002 no.4 pp. 316-317
ISSN:
1364-548X
Subject:
benzoates, chemical reactions, samarium, stereoselectivity
Abstract:
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.
Agid:
6572065