From Radicals to γ-Lactones

From Radicals to γ-Lactones

Author: Theresa Kueckmann

Published Date: 08 May 2012

Source / Publisher: Chemistry An Asian Journal/Wiley-VCH

Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Volatile γ-lactones are popular components of flavorings and fragrances, but their synthesis from O-allyl-α-haloesters by radical cyclization is hindered by slow conformational equilibration.

Fabrice Dénès and co-workers, Université de Nantes, France, have shown that α-bromo aluminum acetals, prepared from the corresponding α-bromo esters using diisobutylaluminum hydride (also known as DIBAL-H) can be cyclized at low temperature under reducing conditions. They report that this method can be combined in a one-pot sequence with subsequent Oppenauer oxidation to prepare the desired γ-lactones. This process enables straightforward access to γ-lactones from easily available precursors. The efficiency of the methodology was illustrated by synthesis of optically enriched (–)-trans-cognac lactone (pictured).