Category: copper-catalyst. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (S)-2-(3-Chloro-2-hydroxypropyl)isoindoline-1,3-dione, is researched, Molecular C11H10ClNO3, CAS is 148857-42-5, about Taking advantage of lithium monohalocarbenoid intrinsic α-elimination in 2-MeTHF: controlled epoxide ring-opening en route to halohydrins. Author is Ielo, Laura; Miele, Margherita; Pillari, Veronica; Senatore, Raffaele; Mirabile, Salvatore; Gitto, Rosaria; Holzer, Wolfgang; Alcantara, Andres R.; Pace, Vittorio.
A straightforward preparation of different β-halohydrins RCR1(OH)CH2X [R = Ph, 4-ClC6H4, 1,3-dioxoisoindolin-2-yl, etc.; R1 = H, Me, CF3, Ph; X = Cl, Br, I] through boosted Kirmse’s elimination of the corresponding lithium monohalocarbenoids starting from epoxide. Crucial for the development of the method was 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 chem. integrity of the carbenoid. The uniformly high-yield, the full preservation of the embodied stereochem. information and the high regiocontrol – deduced by selectively preparing variously decorated motifs further document the potential of this operationally simpleand intuitive methodol.
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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”