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Synthetic routes for a variety of halogenated (chiral) acetic acids from diethyl malonate†
Manuel R. Mazenauer,Stole Manov,Vanessa M. Galati,Philipp Kappeler
RSC Advances Pub Date : 12/07/2017 00:00:00 , DOI:10.1039/C7RA09727A
Abstract

Chiral halomethane is the smallest stable molecule with a single asymmetric C-atom and halogenated acetic acids often serve as precursors. We focus on a synthetic route to synthesise chiral halogenated acetic acids with F, Cl, Br, and H/D isotopic substitution at the α-C-atom starting from diethyl malonate. This reactant is easily available, cheap and allows the obtainment of target acids in a few reaction steps with great versatility. Among all of the possible fully halogenated acetic acids (more than one hundred, which are, in principle, accessible by this route), there are only a small number of chiral halogenated acetic acids, which have been synthesized following the devised synthetic route.

Graphical abstract: Synthetic routes for a variety of halogenated (chiral) acetic acids from diethyl malonate
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