844493-27-2Relevant academic research and scientific papers
Regio- and chemoselective intermolecular hydroamination of allyl imines for the synthesis of 1,2-diamines
Ickes, Andrew R.,Ensign, Seth C.,Gupta, Anil K.,Hull, Kami L.
, p. 11256 - 11259 (2014)
The synthesis of 1,2-diamines via a Rh-catalyzed intermolecular hydroamination of N-allyl imines with cyclic amines is presented. Coordinating groups proximal to the olefin bind to the catalyst and promote the transformation. The reaction affords 1,2-diam
Carbonylative C?C Bond Activation of Electron-Poor Cyclopropanes: Rhodium-Catalyzed (3+1+2) Cycloadditions of Cyclopropylamides
Dalling, Andrew G.,Yamauchi, Takayuki,McCreanor, Niall G.,Cox, Lydia,Bower, John F.
, p. 221 - 225 (2018/12/11)
Rh-catalyzed carbonylative C?C bond activation of cyclopropylamides generates configurationally stable rhodacyclopentanones that engage tethered alkenes in (3+1+2) cycloadditions. These studies provide the first examples of multicomponent cycloadditions t
Rhodium-Catalyzed Regiodivergent Hydrothiolation of Allyl Amines and Imines
Kennemur, Jennifer L.,Kortman, Gregory D.,Hull, Kami L.
supporting information, p. 11914 - 11919 (2016/10/06)
The regiodivergent Rh-catalyzed hydrothiolation of allyl amines and imines is presented. Bidentate phosphine ligands with larger natural bite angles (βn ≥ 99°), for example, DPEphos, dpph, or L1, promote a Markovnikov-selective hydrothiolation in up to 88% yield and >20:1 regioselectivity. Conversely, when smaller bite angle ligands (βn ≤ 86°), for example, dppbz or dppp, are employed, the anti-Markovnikov product is formed in up to 74% yield and >20:1 regioselectivity. Initial mechanistic investigations are performed and are consistent with an oxidative addition/olefin insertion/reductive elimination mechanism for each regioisomeric pathway. We hypothesize that the change in regioselectivity is an effect of diverging coordination spheres to favor either Rh-S or Rh-H insertion to form the branched or linear isomer, respectively.
Flexible synthesis of polyfunctionalised 3-fluoropyrroles
Cogswell, Thomas J.,Donald, Craig S.,Marquez, Rodolfo
supporting information, p. 183 - 190 (2015/12/30)
An efficient and selective approach for the synthesis of polyfunctionalised 3-fluoropyrroles has been developed starting from commercial aldehydes. The methodology is concise, efficient and allows for the modular and systematic assembly of polysubstituted 3-fluoropyrroles. This synthesis provides an alternative and highly convergent strategy for the generation of these chemically and biologically important units.
Ruthenium-catalyzed intramolecular hydrocarbamoylation of allylic formamides: Convenient access to chiral pyrrolidones
Armanino, Nicolas,Carreira, Erick M.
supporting information, p. 6814 - 6817 (2013/06/05)
An attractive strategy for the synthesis of saturated nitrogen-containing heterocycles is described herein, involving the implementation of ruthenium-catalyzed intramolecular hydrocarbamoylation of olefins. The process proceeds by formal C-H bond cleavage
PHOSPHORAMIDITE LIGAND AND PRODUCTION METHOD OF ALLYLIC AMINE USING THE SAME
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Page/Page column 10-11, (2009/04/24)
The present invention provides a production method of an allylic amine represented by the formula (III): wherein R3 is as defined in the specification, which comprises reacting by an allylic alcohol represented by the formula (II): wherein Rsu
Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols: Sulfamic acid as ammonia equivalent
Defieber, Christian,Ariger, Martin A.,Moriel, Patricia,Carreira, Erick M.
, p. 3139 - 3143 (2008/03/11)
(Chemical Equation Presented) Two for the price of one: Sulfamic acid serves not only as a nitrogen source but also as an in situ activator of hydroxy groups in the first direct iridium-catalyzed synthesis of primary allylic amines from allylic alcohols (see scheme; cod = cycloocta-1,5-diene). The reaction is catalyzed by a commercially available iridium complex and a phosphoramidite-based bidentate phosphorus-olefin ligand.
