1728-15-0Relevant articles and documents
One-pot synthesis of α-bromoacetals of ketones from secondary alcohols and 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in ethylene glycol
Han, Bingbing,Zheng, Zubiao,Wu, Fang,Wang, Aidong
, p. 2387 - 2394 (2017)
α-Bromoacetals of ketones were prepared from various secondary alcohols with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and ethylene glycol through oxidation, bromination, and acetalization in one pot without the use of other catalysts under mild conditions. The effects of DBDMH, the solvent, and N-bromosuccinimide on the reaction were investigated. Under the optimal conditions, most α-bromoacetals of ketones were obtain in 90–98% yields.
Application of poly(vinylphenyltrimethylammonium tribromide) resin as an efficient polymeric brominating agent in the α-bromination and α-bromoacetalization of acetophenones
Han, Bingbing,Zheng, Zubiao,Zheng, Dongcheng,Zhang, Lei,Cui, Peng,Shi, Jianjun,Li, Changjiang
supporting information, p. 2512 - 2520 (2019/07/04)
The applications of a new supported tribromide reagent based on poly(vinylbenzyltrimethylammonium hydroxide) resin (Amberlite 717) were reported. This supported tribromide resin was used directly in α-bromination and α-bromoacetalization of acetophenones without any other catalyst under mild conditions. The effects of solvents and the amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of α-bromo and α-bromoacetal of acetophenones were selectively obtained in excellent yields.
Sc(OTf)3-Catalyzed Addition of Bromomagnesium 2-Vinyloxy Ethoxide to Various Aldehydes Leading to Protected Aldol Products
Quinio, Pauline,Kohout, Laura,Roman, Daniela Sustac,Gaar, Jakob,Karaghiosoff, Konstantin,Knochel, Paul
, p. 1715 - 1719 (2016/07/06)
The addition of bromomagnesium 2-vinyloxy ethoxide to various aldehydes in the presence of 10 mol% Sc(OTf)3 provides a broad range of functionalized protected aldol compounds. The enantioselective preparation of these aldols can be achieved via a Swern oxidation-CBS reduction sequence. Use of the dioxolane derived from 2-bromocyclohexanone provides the expected aldol product as the anti diastereoisomer (dr >99:1).