62559-37-9Relevant academic research and scientific papers
Metal-free, one-pot, sequential protocol for transforming ,-epoxy ketones to -hydroxy ketones and -methylene ketones
Hasegawa, Eietsu,Arai, Saki,Tayama, Eiji,Iwamoto, Hajime
, p. 1593 - 1600 (2015/02/19)
A new sequential, one-pot protocol for transforming 1,3-disubstituted 2,3-epoxy ketones to β;-hydroxy ketones and α-methylene ketones has been developed. Reaction of epoxy ketones with boron trifluoride etherate (BF3·OEt2) generates the cationic intermediates by regioselective epoxide ring opening and an acyl shift. Then, a treatment of these cations with 2-aryl-1,3-dimethylbenzimidazolines (DMBIH) results in formation of 1,2-disubstituted 3-hydroxy ketones. DMBIH serves as a hydride donor in the second step of this process. Finally, the β;-hydroxy ketones can be converted to 1,2-disubstituted 2-methylene ketones by treatment with methanesulfonic acid or a combination of methanesulfonyl chloride and triethylamine. Importantly, the sequential steps involved in formation of the α-methylene ketone products can be carried out in one pot.
Titanocene-promoted intermolecular couplings of epoxides with nitriles. An easy access to β-hydroxyketones
Fernandez-Mateos,Encinas Madrazo,Herrero Teijon,Rubio Gonzalez
supporting information; experimental part, p. 3913 - 3918 (2009/10/20)
(Chemical Equation Presented) Radical couplings of epoxides and nitriles mediated by Cp2TiCl provide a diastereoselective route to the synthesis of β-hydroxyketones. The conditions of this "aldol- like" reaction are mild enough to avoid the dehydration of the β-hydroxyketone. The scope of the coupling reaction with functionalized and tetrasubstituted epoxides has been studied. The radical character of the coupling reactions is demonstrated.
Stereoselective Construction of Quaternary Centres at Ambient Temperature by the Highly Stereocontrolled Migration of Groups Containing sp-, sp2-, and sp3-Hybridized Carbon Atoms
Marson, Charles M.,Walker, Andrew J.,Pickering, Jane,Hobson, Adrian D.,Wrigglesworth, Roger,Edge, Simon J.
, p. 5944 - 5951 (2007/10/02)
A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migration groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl
