173066-84-7

Upstream product

• 6169-06-8 (S)-2-Octanol 
• 34817-25-9 (S)-1-methylheptyl tosylate 
• 829-85-6 diphenylphosphane 
• 592-41-6 1-hexene 
• 38828-07-8 diphenyl(α-hydroxy)ethylphosphine oxide 
• 4559-70-0 Diphenylphosphine oxide 

Relevant academic research and scientific papers

Nickel-Catalyzed Enantioconvergent Reductive Hydroalkylation of Olefins with α-Heteroatom Phosphorus or Sulfur Alkyl Electrophiles

Substantial advances in enantioconvergent C(sp3)-C(sp3) bond formation reactions have been made in recent years through the use of transition-metal-catalyzed cross-coupling reactions of racemic secondary alkyl electrophiles with organometallic reagents. Herein, we report a general process for the asymmetric construction of alkyl-alkyl bonds adjacent to heteroatoms, namely, a nickel-catalyzed enantioconvergent reductive hydroalkylation of olefins with α-heteroatom phosphorus or sulfur alkyl electrophiles. Including the use of readily available olefins, this reaction has considerable advantages, such as mild reaction conditions, a broad substrate scope, and good functional group compatibility, making it a desirable alternative to traditional electrophile-nucleophile cross-coupling reactions.

Investigation of the configurational stability of lithiated phosphine oxides using diastereomerically pure and enantiomerically enriched phosphine oxides

Lithiation of racemic but diastereomerically pure phosphine oxides followed by electrophilic quench indicates that lithiated phosphine oxides are not configurationally stable over a period of minutes in THF at -78°C. These results have been verified using an optically active phosphine oxide: lithiation and in situ quench experiments with Me3SiCl and cyclobutanone indicate that the lithium derivatives are not configurationally stable even on the timescale of their reaction with these electrophiles.

On the configurational stability of lithiated phosphine oxides

Two methods have been used to determine whether lithiated phosphine oxides are configurationally stable in THF at -78°C: from both, we conclude that lithiated phosphine oxides are not configurationally stable even on the timescale of reaction with internal electrophiles (eg Me3SiCl).