Literature DB >> 22556018

A convenient access to γ-lactones from O-allyl-α-bromoesters using a one-pot ionic-radical-ionic sequence.

Romain Bénéteau1, Jacques Lebreton, Fabrice Dénès.   

Abstract

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.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2012        PMID: 22556018     DOI: 10.1002/asia.201200212

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  2 in total

1.  The Reaction of β,γ-Epoxy Alcohols with Titanium(III) Reagents. A Proposed Role for Intramolecular Hydrogen Bonding.

Authors:  Sven Klare; Jonathan P Gordon; Andreas Gansäuer; T V RajanBabu; William A Nugent
Journal:  Tetrahedron       Date:  2019-10-01       Impact factor: 2.457

2.  Radical-Mediated Reactions of α-Bromo Aluminium Thioacetals, α-Bromothioesters, and Xanthates for Thiolactone Synthesis.

Authors:  Ruairí O McCourt; Fabrice Dénès; Eoin M Scanlan
Journal:  Molecules       Date:  2018-04-13       Impact factor: 4.411

  2 in total

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