Issue 7, 2015
From the journal:

Organic & Biomolecular Chemistry

In situ intramolecular catalytic 1,2-addition of allenoates to cyclic ketones towards polycyclic allenoates†

Clément F. Heinrich,a   Michel Miescha  and  Laurence Miesch*a  

* Corresponding authors

a Université de Strasbourg, Institut de Chimie, UMR Unistra-CNRS 7177, Laboratoire de Chimie Organique Synthétique, 1 rue Blaise Pascal, BP296/R8, 67008-Strasbourg, France
E-mail: lmiesch@unistra.fr

Abstract

Sequential deprotonation, isomerization of 3-alkynoates and subsequent 1,2-addition led to bicyclic allenoate in the presence of a catalytic amount of Cs2CO3. Cyclization proceeds in a totally stereoselective manner in the case of the two-carbon linker chain. A one-pot reaction starting from alkynyl ketones afforded tricyclic fused ring systems with good yields.

Graphical abstract: In situ intramolecular catalytic 1,2-addition of allenoates to cyclic ketones towards polycyclic allenoates

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Article information

DOI
https://doi.org/10.1039/C4OB02451F
Article type
Paper
Submitted
21 Nov 2014
Accepted
11 Dec 2014
First published
11 Dec 2014

Org. Biomol. Chem., 2015,13, 2153-2156

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In situ intramolecular catalytic 1,2-addition of allenoates to cyclic ketones towards polycyclic allenoates

C. F. Heinrich, M. Miesch and L. Miesch, Org. Biomol. Chem., 2015, 13, 2153 DOI: 10.1039/C4OB02451F

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