794513-19-2Relevant academic research and scientific papers
Catalytic Generation and Chemoselective Transfer of Nucleophilic Hydrides from Dihydrogen
Pape, Felix,Brechmann, Lea T.,Teichert, Johannes F.
, p. 985 - 988 (2019/01/04)
Copper(I)–N-heterocyclic-carbene (NHC) complexes enabled the catalytic generation of nucleophilic hydrides from dihydrogen (H2) and their subsequent transfer to allylic chlorides. The highly chemoselective catalyst displayed no concomitant hydrogenation reactivity; in fact, the terminal double bond formed in the hydride transfer remained intact. Switching to deuterium gas (D2) allowed for regioselective monodeuteration with excellent isotope incorporation.
Stereoselective alkyne semihydrogenations with an air-stable copper(i) catalyst
Thiel, Niklas O.,Teichert, Johannes F.
, p. 10660 - 10666 (2016/11/30)
An air-stable and preactivated copper(i) hydroxide/N-heteroyclic carbene (NHC) complex for alkyne semihydrogenations is reported. Next to an enhanced practicability of the process, the resulting alkenes are obtained with high Z-selectivities and no overreduction to the corresponding alkanes.
Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation
Kyne, Robert E.,Ryan, Michael C.,Kliman, Laura T.,Morken, James P.
supporting information; experimental part, p. 3796 - 3799 (2010/10/21)
Addition of nitrosobenzene to pinacol allylboronates leads to oxidation of the organoboron with concomitant rearrangement of the substrate alkene. This reaction appears to proceed by allylboration of the nitroso group in analogy to carbonyl and imine allylation reactions. Remarkably, the N-O bond is cleaved during the reaction such that simple alcohols are the final reaction product.
Synthesis of nearly enantiopure allylic amines by aza-Claisen rearrangement of Z-configured allylic trifluoroacetimidates catalyzed by highly active ferrocenylbispalladacycles
Jautze, Sascha,Seiler, Paul,Peters, Rene
supporting information; experimental part, p. 1430 - 1444 (2009/04/06)
The development of the first highly active enantioselective catalyst for the aza-Claisen rearrangement of Z-configured allylic trifluoroacetimidates generating valuable almost enantiopure protected allylic amines is described. Usually Z-configured allylic
Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide
Schomaker, Jennifer M.,Pulgam, Veera Reddy,Borhan, Babak
, p. 13600 - 13601 (2007/10/03)
Nucleophilic substitution reactions of 2,3-epoxy alcohols, easily prepared via Sharpless asymmetric epoxidation chemistry, offer access to a wide variety of enantiomerically pure compounds. In this communication, we describe the use of a Payne rearrangement to control regioselectivity in the ring-opening of a series of 2,3-epoxy alcohols with dimethylsulfoxonium methylide to yield diastereomerically and/or enantiomerically pure disubstituted tetrahydrofuran rings. The factors influencing the success and substitution pattern of the THF ring products are discussed, including steric, electronic, and solvent effects. Copyright
