42817-44-7

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 68-12-2 N,N-dimethyl-formamide 
• 100-59-4 phenylmagnesium chloride 
• 124-40-3 dimethyl amine 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 14674-28-3 N-benzylidene-2-methylbenzenesulfonamide 
• 205582-30-5 [(dimethylamino)ethyl]triphenylphosphonium bromide 
• 2568-65-2 N,N-dimethyl-3-phenyl-2-propyn-1-amine 
• 79750-53-1 (E)-3-(4-nitrophenyl)prop-2-en-1-yl bromide 
• 35271-56-8 (E)-4-nitrocinnamyl alcohol 
• 555-16-8 4-nitrobenzaldehdye 
• 24393-61-1 ethyl (E)-3-(4-nitrophenyl)-2-propenoate 
• 102-92-1 Cinnamoyl chloride 
• 2757-10-0 (E)-N-methyl-3-phenyl-acrylamide 

Downstream Products

• 79840-93-0 trans-cinnamyldimethyl-(3,3-dimethyl-2-oxobutyl)ammonium bromide 
• 16241-04-6 O-phenyl N,N-dimethylthiocarbamate 
• 1581720-49-1 C₂₀H₂₄N₂O 
• 1581720-07-1 (2S,3S)-N-benzyl-2-(dimethylamino)-3-phenylpent-4-enamide 
• 1581720-10-6 (2S,3S)-2-(dimethylamino)-N-methoxy-N-methyl-3-phenylpent-4-enamide 
• 1581720-12-8 (2S,3S)-2-(dimethylamino)-3-phenyl-1-(pyrrolidin-1-yl)pent-4-en-1-one 
• 1581720-14-0 (2S,3S)-methyl 2-(dimethylamino)-3-phenylpent-4-enoate 
• 1581720-16-2 (2S,3S)-2-(dimethylamino)-3-phenylpent-4-en-1-ol 

Relevant academic research and scientific papers

Method for preparing tertiary amine organic compound from photocatalytically decomposing substituted formamide

The invention discloses a method for preparing a tertiary amine compound from aldehyde and substituted formamide under the action of a photocatalyst. The method is characterized in that the reaction can be performed only by illumination under the conditions of no hydrogen and no reducing agent. The method is suitable for various aldehydes including aromatic aldehydes, fatty aldehydes and the like,has the characteristics of few byproducts and high product yield, does not need to use hydrogen in the reaction, avoids the use of noble metal hydrogenation catalysts, and has obvious technical and economic effects and application prospects.

Synthesis of tertiary amines by direct Br?nsted acid catalyzed reductive amination

Tertiary amines are ubiquitous and valuable compounds in synthetic chemistry, with a wide range of applications in organocatalysis, organometallic complexes, biological processes and pharmaceutical chemistry. One of the most frequently used pathways to synthesize tertiary amines is the reductive amination reaction of carbonyl compounds. Despite developments of numerous new reductive amination methods in the past few decades, this reaction generally requires non-atom-economic processes with harsh conditions and toxic transition-metal catalysts. Herein, we report simple yet practical protocols using triflic acid as a catalyst to efficiently promote the direct reductive amination reactions of carbonyl compounds on a broad range of substrates. Applications of this new method to generate valuable heterocyclic frameworks and polyamines are also included.

Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts

Herein we report the first highly enantioselective allenoate-Claisen rearrangement using doubly axially chiral phosphate sodium salts as catalysts. This synthetic method provides access to β-amino acid derivatives with vicinal stereocenters in up to 95percent ee. We also investigated the mechanism of enantioinduction by transition state (TS) computations with DFT as well as statistical modeling of the relationship between selectivity and the molecular features of both the catalyst and substrate. The mutual interactions of charge-separated regions in both the zwitterionic intermediate generated by reaction of an amine to the allenoate and the Na+-salt of the chiral phosphate leads to an orientation of the TS in the catalytic pocket that maximizes favorable noncovalent interactions. Crucial arene-arene interactions at the periphery of the catalyst lead to a differentiation of the TS diastereomers. These interactions were interrogated using DFT calculations and validated through statistical modeling of parameters describing noncovalent interactions.

Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides

A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-Allyl ammonium ylides, affording products in up to 95percent isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For

Cobalt-catalyzed (Z)-selective semihydrogenation of alkynes with molecular hydrogen

Cobalt-catalyzed highly (Z)-selective semihydrogenation of alkynes using molecular H2 was developed using commercially available and cheap cobalt precursors. A variety of (Z)-alkenes were obtained in moderate to excellent selectivities [(Z)-alkene/(E)-alkene/alkane ratio up to >99 : 1 : 1] and it was found that the readily available ethylenediamine ligand is crucial in determining the selectivity.

An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides

Benzotetramisole promotes the catalytic asymmetric [2,3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-α-amino acid derivatives with excellent diastereo- and enantioselectivity (up to >95:5 dr; up to >99% ee).

Transformations of dialkyl(4-hydroxy-2-butynyl)-(3-phenylallyl)ammonium bromides in an KOH aqueous solution or in the presence of powdered KOH

Under the action of a twofold excess of KOH and heating in aqueous solution, and also under the conditions of the Stevens rearrangement (with KOH powder and a small amount of methanol) dialkyl-(4-hydroxy-2-butynyl)(3- phenylallyl)ammonium bromides form dialkyl[4-(1-phenylallyl)-2,5-dihydro-2- furyl]amines. Rearrangement-cleavage reaction also occurs under the same conditions.

Tunable stereoselective alkene synthesis by treatment of activated imines with nonstabilized phosphonium ylides

A broad range of readily accessible N-sulfonyl imines undergo olefination reaction with nonstabilized phosphonium ylides under mild conditions to afford an array of both Z- and E-isomers of 1,2-disubstituted alkenes, allylic alcohols, and allylic amines in good yields and with greater than 991 stereoselectivity.

β-regioselective intermolecular Heck arylation of N,N-disubstituted allylamines

β-Regioselectivity has been demonstrated for the Heck arylation of N,N-disubstituted allylamines. The scope and limitations of the reaction were demonstrated by the coupling of N,N-dibenzylallylamine with a variety of substituted aryl triflates. This methodology represents a straightforward approach for the efficient preparation of a variety of primary β-aryl allyl amines.

On the reduction of α,β-unsaturated (Group 6) carbene complexes by NaBH4

Chromium and tungsten styryl Fischer carbene complexes 12 and 15 were transformed into Z-vinyl ether 13 and E-allyl ether 14 by NaBH4 reduction in EtOH. Deuterium labeling experiments demonstrate that the reaction occurs by the initial addition of the hydride to the carbene carbon atom, followed by a 1,3-rearrangement of the M(CO)5 fragment. The process could involve the participation of an η-allyl chromium intermediate. The reaction is general and has been applied to a series of α,β-unsaturated alkoxy and aminocarbene complexes. In the case of chromium and tungsten alkynyl carbenes 38 and 39, NaBH4 reduction exclusively yields E-allyl ether 14. The intermediacy of an allenyl complex 41 obtained after the 1,3-rearrangement of the metal center is confirmed by deuterium labeling experiments. (C) 2000 Elsevier Science Ltd. All rights reserved.