Issue 40, 2013

Strain-promoted retro-Dieckmann-type condensation on [2.2.2]- and [2.2.1]bicyclic systems: a fragmentation reaction for the preparation of functionalized heterocycles and carbocycles

Abstract

The fragmentation reaction of differently functionalized [2.2.2]- and [2.2.1]bicyclic systems that leads to substituted five membered heterocycles and five/six membered carbocycles is broadly studied. This reaction is carried out through a retro-Dieckmann-type condensation on strained [2.2.1]bicyclic β-ketosulfones and their counterparts β-ketoesters under very mild catalytic acid or basic conditions and short reaction times. The same reaction is also achieved on [2.2.2]bicyclic β-ketosulfones requiring harsher reaction conditions.

Graphical abstract: Strain-promoted retro-Dieckmann-type condensation on [2.2.2]- and [2.2.1]bicyclic systems: a fragmentation reaction for the preparation of functionalized heterocycles and carbocycles

Supplementary files

Article information

Article type
Paper
Submitted
05 Jun 2013
Accepted
19 Aug 2013
First published
19 Aug 2013

Org. Biomol. Chem., 2013,11, 7016-7025

Strain-promoted retro-Dieckmann-type condensation on [2.2.2]- and [2.2.1]bicyclic systems: a fragmentation reaction for the preparation of functionalized heterocycles and carbocycles

E. Moreno-Clavijo, A. J. Moreno-Vargas, A. T. Carmona and I. Robina, Org. Biomol. Chem., 2013, 11, 7016 DOI: 10.1039/C3OB41160E

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