58896-48-3

Upstream product

• 769-25-5 2,4,6-trimethylstyrene 
• 487-68-3 mesytaldehyde 
• 104-94-9 4-methoxy-aniline 
• 1370449-08-3 2',4',6'-trimethyl-4-hydroxystilbene 
• 2101-87-3 p-methoxy-phenylazide 

Downstream Products

• 1435936-24-5 C₁₈H₂₁NO₃ 
• 135569-50-5 cis-1-(p-methoxyphenyl)-3-(methylphenylamino)-4-(2,4,6-trimethylphenyl)-2-azetidinone 

Relevant academic research and scientific papers

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

P-N Cooperative Borane Activation and Catalytic Hydroboration by a Distorted Phosphorous Triamide Platform

Studies of the stoichiometric and catalytic reactivity of a geometrically constrained phosphorous triamide 1 with pinacolborane (HBpin) are reported. The addition of HBpin to phosphorous triamide 1 results in cleavage of the B-H bond of pinacolborane through addition across the electrophilic phosphorus and nucleophilic N-methylanilide sites in a cooperative fashion. The kinetics of this process of were investigated by NMR spectroscopy, with the determined overall second-order empirical rate law given by ν = -k[1][HBpin], where k = 4.76 × 10-5 M-1 s-1 at 25 °C. The B-H bond activation process produces P-hydrido-1,3,2-diazaphospholene intermediate 2, which exhibits hydridic reactivity capable of reacting with imines to give phosphorous triamide intermediates, as confirmed by independent synthesis. These phosphorous triamide intermediates are typically short lived, evolving with elimination of the N-borylamine product of imine hydroboration with regeneration of the deformed phosphorous triamide 1. The kinetics of this latter process are shown to be first-order, indicative of a unimolecular mechanism. Consequently, catalytic hydroboration of a variety of imine substrates can be realized with 1 as the catalyst and HBpin as the terminal reagent. A mechanistic proposal implicating a P-N cooperative mechanism for catalysis that incorporates the various independently verified stoichiometric steps is presented, and a comparison to related phosphorus-based systems is offered.

A synthesis of α-amino acids via direct reductive carboxylation of imines with carbon dioxide

A method for the synthesis of α-amino acids by direct reductive carboxylation of aromatic imines with CO2 is described. The protocol employs readily available commercial reagents and serves as a one-step alternative to the Strecker synthesis. The Royal Society of Chemistry 2013.

On the additions of lithium methyl p-tolyl sulfoxide to N-(PMP)arylaldimines

The results presented in this paper confirm that the stereochemical outcome of the reversible additions of lithium (R)-methyl p-tolyl sulfoxide to N-arylidene-p-anisidines (N-PMP imines) depends on: (a) the reaction conditions used and (b) the electronic properties of the arylidene moiety on the starting imine. In particular, we show that under kinetic control (-70 °C) the additions involving electron-rich N-arylidene groups occur with very high stereocontrol in favor of the (2S,RS)-diastereomers, whereas an electron-deficient group favors the opposite stereochemical outcome. Based on the observations above, a mechanistic hypothesis is proposed.

Cycloaddition of (N-Alkyl-N-phenylamino)ketene with Imines

(N-Alkyl-N-phenylamino)ketenes were prepared in the presence of various imines, and a cycloaddition reaction occurred to yield 3-(N-alkyl-N-phenylamino)-2-azetidinones.The size and electronic nature of the imine substituents were varied in order to probe those factors that influence the stereochemistry of the cycloaddition.The stereochemistry of the 2-azetidinone was determined by the substitution pattern of the imines.In general, the stereochemistry of the 2-azetidinone products are significantly influenced by the bulk of the N substituent on the imine.These results are discussed in terms of a two-step zwitterionic intermediate.