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Regiospecific formal [3 + 2] annulation of tert-propargyl alcohols with acyclic 1,3-diketones via the cycloisomerization of homoallenyl ketones

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Abstract

A one-pot, regiospecific synthesis of dihydrofurans bearing a quaternary centre and tetrasubstituted furans is developed from the formal [3 + 2] annulation of tert-propargyl alcohols and 1,3-diketones under Ca(II)/DBU conditions. The reaction proceeds through the SN2I mechanism to form homoallenyl ketone and a subsequent cycloisomerization to yield novel and new chemical entities of privileged scaffolds.

Graphical abstract: Regiospecific formal [3 + 2] annulation of tert-propargyl alcohols with acyclic 1,3-diketones via the cycloisomerization of homoallenyl ketones

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Publication details

The article was received on 01 Sep 2018, accepted on 26 Sep 2018 and first published on 27 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB02158A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Regiospecific formal [3 + 2] annulation of tert-propargyl alcohols with acyclic 1,3-diketones via the cycloisomerization of homoallenyl ketones

    S. Yaragorla and P. Rajesh, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02158A

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