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Intermolecular Radical Reaction of O,Se-Acetals Generated via Seleno-Pummerer Rearrangement

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journal contribution
posted on 03.08.2012 by Daisuke Urabe, Hiroki Yamaguchi, Ayumi Someya, Masayuki Inoue
A new general protocol for the synthesis of O,Se-acetals using the seleno-Pummerer reaction has been developed, and their radical-based two- and three-component coupling reactions were studied. The three-component coupling employed the O,Se-acetal, cyclopentenone, and an allylstannane derivative, and enabled stereoselective installations of α-acyloxy alkyl and functionalized allyl groups to generate the 2,3-trans-disubstituted cyclopentanone in a single operation. The obtained highly functionalized structure was used as an intermediate for facile assembly of the zedoarondiol carboskeleton.

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