Issue 9, 2021

Taking advantage of lithium monohalocarbenoid intrinsic α-elimination in 2-MeTHF: controlled epoxide ring-opening en route to halohydrins

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.

Graphical abstract: Taking advantage of lithium monohalocarbenoid intrinsic α-elimination in 2-MeTHF: controlled epoxide ring-opening en route to halohydrins

Supplementary files

Article information

Article type
Paper
Submitted
02 Dec 2020
Accepted
08 Jan 2021
First published
08 Jan 2021

Org. Biomol. Chem., 2021,19, 2038-2043

Taking advantage of lithium monohalocarbenoid intrinsic α-elimination in 2-MeTHF: controlled epoxide ring-opening en route to halohydrins

L. Ielo, M. Miele, V. Pillari, R. Senatore, S. Mirabile, R. Gitto, W. Holzer, A. R. Alcántara and V. Pace, Org. Biomol. Chem., 2021, 19, 2038 DOI: 10.1039/D0OB02407D

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