61752-45-2Relevant academic research and scientific papers
Prins cyclization of α-bromoethers under basic conditions
Arpin, Patrice,Hill, Bryan,Larouche-Gauthier, Robin,Spino, Claude
, p. 1193 - 1201 (2014/01/06)
α-Bromoethers have been found to undergo Prins-type cyclization under basic conditions and without the need to add a promoter. The products are those derived from a Markovnikov addition on the pendant alkene. However, the stereochemistry and even the structure of the products sometimes differ from those expected with the classical Lewis-acid-catalyzed Prins reaction of acetals.
A new zincate-mediated rearrangement reaction of 2-(1-hydroxyalkyl)-1- alkylcyclopropanol
Nomura, Kenichi,Matsubara, Seijiro
scheme or table, p. 703 - 708 (2010/08/05)
A novel rearrangement of 2-(1-hydroxyalkyl)-1-alkylcyclopropanol has been found. It proceeds in the presence of a catalytic amount of organozinc ate complex to give vic-diols. The rearrangement can be applied to various types of 2-(1-hydroxyalkyl)-1-alkyl-cyclopropanol, which can be easily prepared from the corresponding α,β-ep-oxyketones and bis(iodozincio)methane. When bicyclo[13.1.0]-pentadecane-1, 15-diol was treated with the organozinc ate complex, the corresponding 14-membered cyclic vic-diol was obtained. Thus, this rearrangement is also useful for changing the ring size of cyclic substrates.
Stereoselective synthesis of β,γ-unsaturated ketones by acid-mediated Julia-type transformation from 2-(1-hydroxyalkyl)-1- alkylcyclopropanols
Nomura, Kenichi,Matsubara, Seijiro
experimental part, p. 1412 - 1414 (2009/04/06)
An efficient transformation of 2-(1-hydroxyalkyl)-1-alkylcyclopropanols, obtained from α,β-unsaturated ketones, to β,γ-unsaturated ketones was achieved by trifluoroacetic acid (TFA)-mediated reaction. Georg Thieme Verlag Stuttgart.
Reduction of 4,5-Dihydro-1,2-oxazoles (Δ2-Isoxazolines); A Cycloadditive Approach to 2-Alkenyl Ketones
Curran, Dennis P.,Kim, Byeang Hyean
, p. 312 - 315 (2007/10/02)
A new cycloadditive route to 2-alkenyl ketones (β,γ-unsaturated ketones) involves: (1) nitrile oxide-allylsilane (or stannane) cycloaddition, (2) reductive cleavage of the resultant isoxazoline, and (3) Peterson elimination.In all cases, the products are not contaminated by the isomeric 1-alkenyl ketones.Although stereoselectivity in the nitrile oxide cycloaddition to 3-trimethylsilyl-1-butene is low, the resultant diastereomeric cycloadducts can be converted stereospecifically to the corresponding (E)- and (Z)-olefins.
