Taking advantage of lithium monohalocarbenoid intrinsic α-elimination in 2-MeTHF: controlled epoxide ring-openingen routeto halohydrins

Laura Ielo, Margherita Miele, Veronica Pillari, Raffaele Senatore, Salvatore Mirabile, Rosaria Gitto, Wolfgang Holzer, Andrés R. Alcántara, Vittorio Pace (Corresponding author)

Publications: Contribution to journalArticlePeer Reviewed

Abstract

The intrinsic degradative α-elimination of Li carbenoids somehow complicates their use in synthesis as C1-synthons. Nevertheless, we herein report how boosting such an α-elimination is a straightforward strategy for accomplishing controlled ring-opening of epoxides to furnish the corresponding β-halohydrins. Crucial for the development of the method is the use of the eco-friendly solvent 2-MeTHF, which forces the degradation of the incipient monohalolithium, due to the very limited stabilizing effect of this solvent on the chemical integrity of the carbenoid. With this approach, high yields of the targeted compounds are consistently obtained under very high regiocontrol and, despite the basic nature of the reagents, no racemization of enantiopure materials is observed.

Original languageEnglish
Pages (from-to)2038-2043
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number9
DOIs
Publication statusPublished - 7 Mar 2021

Austrian Fields of Science 2012

  • 104015 Organic chemistry

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