4566-58-9

Upstream product

• 13787-96-7 (rac)-exo-2,3,5-triphenylisoxazolidine 
• 201024-81-9 C,N-diphenylnitrone 
• 100-42-5 styrene 
• 742-43-8 1,3-diphenyl-3-(N-phenylamino)propanone 
• 17714-40-8 1,3-Dibromo-1,3-diphenylpropane 
• 586-96-9 Nitrosobenzene 
• 193537-12-1 1-Phenyl-N-phenyl-2-phenylsulfanylethylamine 
• 538-51-2 benzylidene phenylamine 
• 13787-96-7 2,3,5-Triphenylisoxazolidine 
• 100-52-7 benzaldehyde 
• 624-92-0 Dimethyldisulphide 
• 55552-57-3 C₁₄H₁₄BrHgN 

Relevant academic research and scientific papers

Direct introduction of nitrogen and oxygen functionality with spatial control using copper catalysis

Synthetic chemists have spent considerable effort optimizing the synthesis of nitrogen and oxygen containing compounds through a number of methods; however, direct introduction of N- and O-functionality remains challenging. Presented herein is a general method to allow for the simultaneous installation of N- and O-functionality to construct unexplored N-O heterocyclic and amino-alcohol scaffolds. This transformation uses earth abundant copper salts to facilitate the formation of a carbon-centered radical and subsequent carbon-nitrogen bond formation. The intermediate aminoxyl radical is terminated by an intramolecularly appended carbon-centered radical. We have exploited this methodology to also access amino-alcohols with a range of aliphatic and aromatic linkers.

Water promoted iodotrimethyl silane reactions: Reductive cleavage of isoxazolidines and 2,1-benzisoxazoles to γ-amino alcohols and o-aminobenzophenones

Water promoted iodotrimethyl silane [ITMS] reductively cleaved isoxazolidines and 2,1-benzisoxazoles to γ-amino alcohols and o-aminobenzophenones respectively at shorter times and in higher yields at room temperature.

Zn-AlCl3.6H2O-THF system: A mild and convenient reducing agent for isoxazolidines to 1,3-amino alcohols

The Zn-AlCl3.6H2O-THF system reduces isoxazolidines to 1,3-amino alcohols at room temperature.

Functionalized organolithium compounds of DTBB-catalyzed sulfur-lithium exchange

The successive reaction of β- or γ-hydroxy or amino phenyl thioethers (1,4) with butyllithium and an excess of lithium powder in the presence of a catalytic amount of DTBB in THF at - 78°C leads to the formation of the corresponding β- or γ-functionalized organolithium compounds 2 or 5, respectively, which by treatment with different electrophiles [D2O, t- BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO] at temperatures ranging between - 78°C and room temperature yields, after hydrolysis with water, the expected functionalized alcohols or amines 3 or 6, respectively, in a completely regioselective manner.

β-Functionalised organolithium compounds through a sulfur-lithium exchange

The successive reaction of different β-hydroxy or β-amino tbioethers 1a-d with n-butyl-lithium and an excess of lithium powder and a catalytic amount of DTB in THF at -78°C leads to the formation of the corresponding β-functionalised organolithium compounds 2a-d, which by reaction with several electrophiles [D2O, Bu(t)CHO, PhCHO, Me2CO, (CH2)5CO] at temperatures ranging between -78 and 20°C yields, after hydrolysis with water, the expected functionalised alcohols or amines 3aa-de in a regioselective manner.

Diastereoselective Reduction of Acyclic N-Aryl-β-amino Ketones

A stereoselective route to anti- and syn-N-aryl-γ-amino alcohols is reported featuring the reduction of the corresponding β-amino ketones with Et3BHLi or Zn(BH4)2, respectively.

β-Substituted Organolithium Compounds. Reaction with Alkyl Halides, Dimethyl Disulfide, and Imines

The reaction of β-substituted organolithium derivatives with several electrophiles leads to mono- as well as bifunctionalized organic compounds.Thus, by treatment of these dianions with alkyl halides a direct attack on the carbanionic carbon atom is performed, giving as a result substituted amines.When dimethyl disulfide is used, β-amino and β-hydroxy thioethers are obtained.Finally, on reaction with imines, 1-amino-3-hydroxy compounds and 1,3-diamines are obtained.Since these dianions are easily preparated by mercury-lithium transmetalation from β-substituted organomercurials resulting from the addition of mercury(II) salts to olefins, this whole process gives an appropriate way of functionalizing olefins.