41718-52-9Relevant articles and documents
One-pot method for α-phenylation of ketones using isoxazolidine and triphenylaluminum
Miyoshi, Tetsuya,Sato, Shohei,Tanaka, Hiroya,Hasegawa, Chihiro,Ueda, Masafumi,Miyata, Okiko
experimental part, p. 4188 - 4191 (2012/08/28)
The efficient one-pot umpolung α-phenylation of ketones via N-alkenylisoxazolidine is described. When the various ketones are treated with triphenylaluminum prepared from phenylmagnesium chloride and AlCl3 in the presence of isoxazolidine, the desired products are obtained in good to moderate yield. This method is equivalent to a direct α-arylation reaction of carbonyl groups.
Et2Zn-mediated rearrangement of bromohydrins
Li, Lezhen,Cai, Peijie,Guo, Qingxiang,Xue, Song
, p. 3516 - 3522 (2008/09/20)
(Chemical Equation Presented) A simple and highly efficient method for the rearrangement of bromohydrins mediated by Et2Zn to synthesize carbonyl compounds was described. Various β-bromo alcohols were treated with 0.6 equiv of Et2Zn to form a zinc complex in CH 2Cl2 at room temperature for 2 h, followed by 1,2-migration to give the corresponding carbonyl compounds. This remarkable and clean rearrangement is general for acyclic and cyclic bromohydrins, and a variety of ring-expansive and -contractive carbonyl compounds were obtained in good to excellent yields according to the feature of the starting bromohydrins. The functional group tolerance of organozinc reagents in this reaction will be useful in organic synthesis. The scope and limitations of this rearrangement process were also investigated.
