Premium
A Convenient Access to γ‐Lactones from O ‐Allyl‐α‐Bromoesters using a One‐Pot Ionic–Radical–Ionic Sequence
Author(s) -
Bénéteau Romain,
Lebreton Jacques,
Dénès Fabrice
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200212
Subject(s) - chemistry , acetal , sequence (biology) , ionic bonding , radical cyclization , organic chemistry , medicinal chemistry , ion , biochemistry
Cognac in the jar! An efficient one‐pot sequence for the preparation of γ‐lactones is described. Following reduction of α‐bromo ester precursors with DIBAL‐H and radical cyclization of the resulting O ‐aluminum acetals, a preparative in‐situ Oppenauer‐type oxidation of the cyclic O ‐aluminum acetal using simple aldehydes or ketones gives access to γ‐lactones in high yields.