96240-08-3

Upstream product

• 201230-82-2 carbon monoxide 
• 4626-58-8 benzyl(but-2-yn-1-yl)amine 
• 127275-19-8 1-amino>-3-butene 
• 96240-04-9 1-benzyl-4-methylpyrrolidin-2-one 
• 2938-98-9 2-methyl-1,4-butandiol 
• 100-46-9 benzylamine 
• 53215-95-5 N-(trimethylsilylmethyl)benzylamine 
• 75-24-1 trimethylaluminum 
• 92686-95-8 C₁₄H₁₉NO₃ 

Relevant academic research and scientific papers

A New Route to Cyclic Amines by Anionic Cyclization

Transmetallation of an aminomethylstannane gives rise to an aminomethyllithium which undergoes an anionic cyclization onto an unactivated alkene.The resulting organolithium reincorporates trimethyltin to give the product cyclic amine.The cyclization can b

Photoinduced set generation of α-amineradicals: A practical method for the synthesis of pyrrolidines and piperidines

Selective desilylation to generate α-amineradicals from α-alkyl silylamine radical cation and their intramolecular cyclisation is reported.

A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles

An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles.

Stereoselective anionic cyclizations to pyrroldines

Cyclization of α-amino-organolithiums onto unactivated alkenes results in the formation of 2,4-disubstituted pyrrolidines with high selectivities in favour of the cis isomers. The use of the α-methylbenzyl chiral auxiliary on the nitrogen atom gives rise

Synthesis of 3-alkylpyrrolidines by anionic cyclization

α-Aminocarbanions, generated by transmetallation of aminomethylstannaes, cyclize onto an unactivated alkene to give 3-alkylpyrrolidines. The intermediate organolithium either reincorporates trimethyltin or, from the tributylstannanes, can be trapped with a variety of electrophiles. From the trimethylstannane, the cyclization can be promoted catalytically using 0.2 equivalents of methyllithium. The trimethyltin group in the product can be cleaved using ceric ammonium nitrate. Trapping the 3-lithiomethylpyrrolidine with ethylchloroformate, followed by hydrolysis provides a four step synthesis of the GABA uptake inhibitor 3-pyrrolidineacetic acid.

INDOLIZIDINE AND QUINOLIZIDINE RING FORMATION IN THE SET-PHOTOCHEMISTRY OF α-SILYLAMINES

The scope and limitations of indolizidine and quinolizidine ring forming, SET-photoinduced, α-amino radical cyclization reactions were explored.

Photoinduced electron transfer (PET) promoted cyclisations of 1-[N-alkyl-N-(trimethylsilyl)methyl]amines tethered to proximate olefin: Mechanistic and synthetic perspectives

Upon PET reaction, amines of type 1 undergo efficient cyclisations to produce pyrrolidines and piperidines. Mechanistically, involvement of delocalised α-silylmethyl amine radical cation as reactive intermediate in such cyclisations are described.

Rhodium-Catalysed Reactions of Propargylamines with CO/H2. Formation of Pyrroles and Butenolides

Rhodium-catalysed reactions of (arylpropargyl)amines with CO/H2 give β-arylpyrroles in good yields.Reactions of (alkylpropargyl)amines gave alkylpyrroles together with butenolides which are formed in an unusual reaction that probably involves double carbonylation, reduction of one carbonyl function and removal of the amine function by hydrogenolysis.The single-crystal X-ray structure of 5-methyl-N,3-diphenylpyrrole-2-carboxamide is recorded.

The Synthesis of 4-Methyl-2-pyrrolidones and 3-Methyl-1-pyrrolidines and Their Mass Spectral Study

A number of 1-alkyl-4-methyl-2-pyrrolidones have been prepared from methyl 4-alkylamino-3-methyl butenoates.The corresponding 1-alkyl-3-methyl-pyrrolidines are obtainable by the reduction of the pyrrolidones with lithium aluminium hydride.The mass spectra