In 2022,Moschona, Fotini; Misirlaki, Christina; Karadimas, Nikolaos; Koutiva, Maria; Savvopoulou, Ioanna; Rassias, Gerasimos published an article in Symmetry. The title of the article was 《Organocatalytic Asymmetric Halocyclization of Allylic Amides to Chiral Oxazolines Using DTBM-SEGPHOS-Mechanistic Implications from Hammett Plots》.Product Details of 2398-37-0 The author mentioned the following in the article:
The intramol. halocyclization of alkenes possessing an internal heteroatom nucleophile leads to multifunctional heterocycles which are useful versatile intermediates in organic synthesis. The asym. chlorocyclization of 2-substituted allylic amides ArC(O)NHCH2C(=CH2)R (R = Ph, 4-FC6H4, pyridin-3-yl, naphthalen-1-yl, etc.; Ar = Ph, 4-MeOC6H4, 4-MeC6H4, etc.) gives access to chiral oxazolines I (X = Cl) bearing a chloromethyl moiety for further synthetic manipulation. The literature reports on this transformation involve complex syntheses of the 2-substituted allylic amides and cryogenic temperatures for achieving high enantioselectivities in the organocatalyzed halocyclization step. Based on the Heck reaction of aryl bromides ArBr (Ar = Ph, 4-CNC6H4, pyridin-3-yl, naphthalen-1-yl, etc.;) and Boc-protected allylamine or allylamine benzamides, a practical synthesis of 2-substituted allylic amides that does not require chromatog. was developed and accomplished their asym. halocyclization reaction with 24-92%ee under practical conditions (5°C, CpME) catalyzed by (S)-(+)-DTBM-SEGPHOS. In addition, using appropriately substituted substrates, Hammett plots were generated and formulated a consistent mechanism for the halocyclization reaction which involves two competing modes of formation of the haliranium intermediate whose relative kinetics are governed by the electronic properties of the substrate. The experimental process involved the reaction of 1-Bromo-3-methoxybenzene(cas: 2398-37-0Product Details of 2398-37-0)
1-Bromo-3-methoxybenzene(cas: 2398-37-0) can be used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals.Product Details of 2398-37-0
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem