65956-41-4Relevant academic research and scientific papers
Installation of a chiral side chain to a 2-alkylidene-1-cycloalkan-1-ol unit by using allylic substitution
Feng, Chao,Kobayashi, Yuichi
, p. 6666 - 6676 (2013/11/06)
The allylic substitution of optically active exocyclic allylic esters of cyclopentane and cyclohexane with ArMgBr-based copper reagents (Ar = aryl) was examined. ArMgBr/Cu(acac)2 in a 2:1 ratio was an adequate reagent to produce the anti-SN2' products efficiently in terms of regioselectivity (95-99a€‰%), chirality transfer (91-99a€‰%), and yield (71-91a€‰%). The Ar groups that were successfully installed include Ph and p-tolyl, those with electron-donating (i.e., p-MeOC6H4) and electron-withdrawing groups (i.e., p-FC6H4), and those with sterically demanding groups (i.e., o-tolyl, o-MeOC6H 4). In an examination of an alkyl reagent, BuMgBr/CuBr·Me 2S in a 2:1 ratio in the presence of ZnI2 afforded the product with high regioselectivity (99a€‰%) and in good yield (91a€‰%). The allylic substitution of exocyclic allylic picolinates (n = 1, 2; R = Ph(CH2)2, iPr, Ph) with a ArCu(acac)MgBr reagent (Ar = Ph, p-tolyl, p-MeOC6H4, p-FC6H4, o-tolyl, o-MeOC6H4) that was derived from a 2:1 ratio of ArMgBr and Cu(acac)2 efficiently afforded the anti-SN2' products in terms of regioselectivity (95-99a€‰%), chirality transfer (91-99a€‰%), and yield (71-91a€‰%). Copyright
Branch-selective intermolecular hydroacylation: Hydrogen-mediated coupling of anhydrides to styrenes and activated olefins
Hong, Young-Taek,Barchuk, Andriy,Krische, Michael J.
, p. 6885 - 6888 (2007/10/03)
(Chemical Equation Presented) Branching out with hydrogen: Hydrogenation of symmetric or mixed carboxylic anhydrides in the presence of styrenes or activated olefins generates intermolecular hydroacylation products. The use of cationic rhodium catalysts ligated by triphenylarsine (Ph3As) results in the formation of branched coupling products as single regioisomers in high yields (see scheme; cod = cycloocta-1,5-diene, ArF = 3,5-(CF 3)2C6H3).
Conversion of ketone trimethylsilylcyanohydrins to several types of compounds
Ohta,Yamashita,Arita,Kajiura,Kawasaki,Noda,Izumi
, p. 1294 - 1301 (2007/10/02)
Cyclic ketone O-trimethylsilylcyanohydrins (2) were prepared and converted to various compounds: α-hydroxyketones (3), dehydroxylated ketones (4), α,β-unsaturated ketones (9), tricyclic ketones (10), 1-ethoxycarbonyl-4- phenyl-1,2,4a,5,6,7,8,8a-octahydro-2-naphthalenone (13), 1- phenylperhydroisocoumarin (18) and 1,2,3,4,4a,10,11,11a-octahydro-5h- benzo[a,d]cyclohepten-10-one (20).
