Issue 7, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
01 set 2018
Accepted
26 set 2018
First published
27 set 2018

Org. Biomol. Chem., 2019,17, 1924-1928

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., 2019, 17, 1924 DOI: 10.1039/C8OB02158A

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