5801-17-2Relevant articles and documents
Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes
Chen, Shuming,Gieuw, Matthew H.,Houk, K. N.,Ke, Zhihai,Yeung, Ying-Yeung
, p. 9426 - 9433 (2020/10/02)
Although radical formation from a trialkylborane is well documented, the analogous reaction mode is unknown for trihaloboranes. We have discovered the generation of bromine radicals from boron tribromide and simple proton sources, such as water ortert-butanol, under open-flask conditions. Cyclopropanes bearing a variety of substituents were hydro- and deuterio-brominated to furnish anti-Markovnikov products in a highly regioselective fashion. NMR mechanistic studies and DFT calculations point to a radical pathway instead of the conventional ionic mechanism expected for BBr3
Intrazeolite photooxygenation of chiral alkenes. Control of facial selectivity by confinement and cation-π interactions
Stratakis, Manolis,Raptis, Christos,Sofikiti, Nikoletta,Tsangarakis, Constantinos,Kosmas, Giannis,Zaravinos, Ioannis-Panagiotis,Kalaitzakis, Dimitris,Stavroulakis, Dimitris,Baskakis, Constantinos,Stathoulopoulou, Aggeliki
, p. 10623 - 10632 (2007/10/03)
Depending on the nature of the substituents on the stereogenic carbon atom, the ene reaction of singlet oxygen with several chiral alkenes by confinement within thionin-supported zeolite NaY, may exhibit significant changes on facial selectivity by comparison to their photooxygenation reaction in solution. It is proposed that, apart from the conformational consequences as a result of the alkene confinement within the zeolite cavities, a synergism between Na+-π interactions and singlet oxygen-Na+ interactions plays a significant role in the transition states of ene hydroperoxidation. Within NaY, the diastereoselectivity may significantly depend on the site selectivity, as probed through specific deuterium labelling of trisubstituted alkenes bearing a gem-dimethyl group. In certain cases, a remote stereogenic centre relative to the reacting double bond may induce enhanced diastereoselection and regioselectivity.
Ene Reaction Mechanisms. 1. Chirality Transfer to the Enophile 4-Methyl-N-sulfinylbenzenesulfonamide
Bussas, Reinhard,Muensterer, Heribert,Kresze, Guenter
, p. 2828 - 2832 (2007/10/02)
The ene reaction of (S)-(+)-3-phenyl-1-butene (1) with N-sulfinyl-p-toluenesulfonamide (2) leads to the optically active (E)-2-alkenesulfinamide 3.This corresponds to a chirality transfer from the chiral carbon center in 1 to the sulfur atom of the produc