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Issue 12, 2011
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Stereoselective heterocycle synthesis through a reversible allylic alcohol transposition and nucleophilic addition sequence

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Abstract

The abilities of Re2O7 to promote non-stereoselective allylic alcohol transposition reactions and acetal ionization or enone activation have been coupled for a heterocycle synthesis in which thermodynamics dictate stereochemical outcomes. The stabilities of intermediate allylic cation and oxocarbenium ion intermediates dictate the efficiency of product equilibration. Long range stereoinduction can be observed in the synthesis of spiroketals and spirotricycles through this protocol.

Graphical abstract: Stereoselective heterocycle synthesis through a reversible allylic alcohol transposition and nucleophilic addition sequence

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Publication details

The article was received on 16 Aug 2011, accepted on 06 Sep 2011 and first published on 14 Sep 2011


Article type: Edge Article
DOI: 10.1039/C1SC00570G
Citation: Chem. Sci., 2011,2, 2423-2427
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    Stereoselective heterocycle synthesis through a reversible allylic alcohol transposition and nucleophilic addition sequence

    Y. Xie and P. E. Floreancig, Chem. Sci., 2011, 2, 2423
    DOI: 10.1039/C1SC00570G

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