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Issue 5, 2011
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A tandem reaction of organozinc reagent prepared from palladium-catalyzed umpolung method: diastereoselective formation of cyclohexene derivatives bearing three adjacent stereocenters

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Abstract

In the presence of a palladium catalyst, treatment of γ-acyloxy-α,β-unsaturated ketone with bis(iodozincio)methane caused umpolung of π-allylpalladium to give a zinc dienolate. Thus formed zinc species afforded a cyclohexene derivative via a self-condesation reaction. It is noteworthy that the three adjacent stereogenic centers were created in a single process with quite high diastereoselectivity.

Graphical abstract: A tandem reaction of organozinc reagent prepared from palladium-catalyzed umpolung method: diastereoselective formation of cyclohexene derivatives bearing three adjacent stereocenters

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Supplementary files

Article information


Submitted
01 Oct 2010
Accepted
05 Nov 2010
First published
05 Jan 2011

Org. Biomol. Chem., 2011,9, 1389-1393
Article type
Paper

A tandem reaction of organozinc reagent prepared from palladium-catalyzed umpolung method: diastereoselective formation of cyclohexene derivatives bearing three adjacent stereocenters

M. Sada, K. Nomura and S. Matsubara, Org. Biomol. Chem., 2011, 9, 1389
DOI: 10.1039/C0OB00806K

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