123552-75-0

Upstream product

• 100-46-9 benzylamine 
• 122-57-6 1-Phenylbut-1-en-3-one 

Downstream Products

• 174836-57-8 (1-benzyl-2-methyl-4-phenyl-1-azabuta-1,3-diene)tricarbonyliron⁽⁰⁾ 
• 123552-76-1 C₁₇H₁₅⁽²⁾H₂N 
• 5396-91-8 1,5-diphenyl-3-pentanone 
• 2550-26-7 4-Phenyl-2-butanone 
• 122-57-6 1-Phenylbut-1-en-3-one 

Relevant academic research and scientific papers

π-Facial Selectivities in Hydride Reductions of Hindered Endocyclic Iminium Ions

The origins of -facial selectivities in the borohydride reduction of endocyclic iminium ions have been elucidated by density functional theory calculations. In reductions of conjugated ("thermodynamic") iminium ions, the -facial preference of the hydride attack was found to be due to torsional steering. Attack at the favored -face leads to a lower-energy "half-chair"-like conformation of the tetrahydropyridine product, whereas attack at the other -face results in an unfavorable "twist-boat" conformation. In reductions of nonconjugated ("kinetic") iminium ions, torsional distinction is small between the top- A nd bottom-face attacks, and the -facial selectivity of the hydride approach is primarily due to steric hindrance.

Asymmetric metal free β-boration of α,β-unsaturated imines assisted by (S)-MeBoPhoz

The adduct [MeO → Bpin-Bpin]- efficiently mediates the β-boration of α,β-unsaturated imines formed in situ. The use of chiral phosphines as additives, and in particular the chiral phosphine (S)-MeBoPhoz, enables the catalytic asymmetric reactio

Understanding α,β-unsaturated imine formation from amine additions to α,β-unsaturated aldehydes and ketones: An analytical and theoretical investigation

A combination of in situ IR spectroscopy (ReactIR) and DFT calculations have been used to understand what factors govern the selectivity in the addition of primary amines to α,β-unsaturated aldehydes and ketones, i.e., 1,2- versus 1,4-addition. It has been found that the 1,2-addition products (α,β-unsaturated imines following addition and elimination) usually predominate for most systems. However, exceptions, such as methyl vinyl ketone, selectively give 1,4-addition products. This has been rationalized by DFT calculations that show that major conformational effects are involved, controlled mainly by steric effects of carbonyl substituents, resulting in a model that provides simple and predictable preparation of α,β- unsaturated imines for in situ utilization in synthesis.

Highly diastereoselective synthesis of tetrahydropyridines by a C-H activation-cyclization-reduction cascade

A versatile reaction cascade leading to highly substituted 1,2,3,6-tetrahydropyridines has been developed. It comprises rhodium(I)-catalyzed C-H activation-alkyne coupling followed by electrocyclization and subsequent acid/borohydride-promoted reduction. This one-pot procedure affords the target compounds in up to 95% yield with >95% diastereomeric purity.

α-Benzylation of Ketones by Reaction with Benzylamine. Regioselective Reduction of C-C Double Bonds in Cohjugated Enones

Prolonged reaction of some ketones with benzylamine at reflux converts them into α-benzyl derivatives by a route involving Aldol condensation of the related ketimine with benzaldimine followed by exclusive reduction of the resultant C-C double bond.Reduction does not occur when pure benzylamine is used under oxygen-free nitrogen, however the inclusion of a trace of benzaldehyde restores the efficiency of the reaction.Treatment of several ketones in this manner established the scope of the process.When the reaction was extended to the reduction of α,β-unsaturated enones again using benzylamine, reaction times were shorter and the product yield greater.The possibility that the reductive step was an intramolecular 1,5-hydrogen transfer was studied.