51100-54-0Relevant articles and documents
Base-catalysed Rearrangement of β-Hydroxyvinylsilanes to Allyl Silyl Ethers
Sato, Fumie,Tanaka, Youichi,Sato, Masao
, p. 165 - 166 (1983)
A 1,3-silyl group shift from carbon to oxygen occurs readily when β-hydroxyvinylsilanes are treated with catalytic amounts of sodium hydride in hexamethylphosphoric triamide, thus providing the first demonstration of the rearrangement of silicon from sp2-carbon to oxygen.
Using Neighboring-Group Participation for Acyclic Stereocontrol in Diastereoselective Substitution Reactions of Acetals
Ramdular, Amanda,Woerpel, K. A.
supporting information, (2020/06/08)
Neighboring-group participation of an ester enabled stereocontrol in substitution reactions of acyclic acetals. The ester group formed a trans-fused dioxolenium ion intermediate, which underwent a substitution reaction at the acetal carbon atom to afford the product with high diastereoselectivity. Neighboring-group participation was confirmed by isolating dioxolane products resulting from nucleophilic addition at C-2 of a 1,3-dioxolenium ion intermediate. Using a pivaloate ester as the participating group in combination with strong nucleophiles produced substitution products with diastereoselectivities of ≥90:10.
Enantioselective addition of selenosulfonates to α,β-unsaturated ketones
Luo, Shilong,Zhang, Nan,Wang, Zhen,Yan, Hailong
supporting information, p. 2893 - 2901 (2018/05/03)
An organo-catalyzed enantioselective addition of selenosulfonates to α,β-unsaturated ketones was developed for the first time. With a chiral squaramide as an efficient catalyst, the desired α-selenylated ketones were obtained in a good yields with high enantioselectivity up to 89% ee, and good results could be obtained on a gram scale. The products could also be efficiently transformed into useful building blocks with a propenylic stereocenter; the strategy presented in this study may find further applications in organic synthesis.
Solvent-Free Aerobic Epoxidation of Dec-1-ene Using Gold/Graphite as a Catalyst
Gupta, Upendra Nath,Dummer, Nicholas F.,Pattisson, Samuel,Jenkins, Robert L.,Knight, David W.,Bethell, Donald,Hutchings, Graham J.
, p. 689 - 696 (2015/08/04)
The oxidation of dec-1-ene has been investigated using gold nanoparticles supported on graphite in the presence of a radical initiator (α,α-azobisisobutyronitrile) using oxygen from air as oxidant. We have investigated the influence of the reaction temperature (70-100 °C), catalyst mass and reaction time on the epoxide yield. In the absence of a radical initiator the reaction does not proceed, although auto-oxidation can occur at higher temperatures in the range studied. However, in the presence of an initiator, selective oxidation occurs and the initiator propagates the reaction through the formation of a peroxy-radical at the allylic C3 position. Graphite enhances the formation of the allylic products dec-1-en-3-ol, dec-1-en-3-one, and dec-2-en-1-ol; however, the addition of gold nanoparticles to the graphite, enhances formation of 1,2-epoxydecane. It is suggested that gold suppresses the formation of allylic products via a Russell termination. Graphical Abstract: [Figure not available: see fulltext.]
