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Issue 1, 2012
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Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems

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Abstract

A general method for the synthesis of β-substituted and unsubstituted cycloheptenones bearing enantioenriched all-carbon γ-quaternary stereocenters is reported. Hydride or organometallic addition to a seven-membered ring vinylogous ester followed by finely tuned quenching parameters achieves elimination to the corresponding cycloheptenone. The resulting enones are elaborated to bi- and tricyclic compounds with potential for the preparation of non-natural analogs and whose structures are embedded in a number of cycloheptanoid natural products.

Graphical abstract: Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems

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Publication details

The article was received on 17 Jul 2011, accepted on 27 Aug 2011 and first published on 01 Sep 2011


Article type: Paper
DOI: 10.1039/C1OB06189E
Citation: Org. Biomol. Chem., 2012,10, 56-59
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    Synthesis of enantioenriched γ-quaternary cycloheptenones using a combined allylic alkylation/Stork–Danheiser approach: preparation of mono-, bi-, and tricyclic systems

    N. B. Bennett, A. Y. Hong, A. M. Harned and B. M. Stoltz, Org. Biomol. Chem., 2012, 10, 56
    DOI: 10.1039/C1OB06189E

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