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Upstream product

• 100-42-5 styrene 
• 57402-97-8 N-<(trimethylsilyl)methyl>benzaldimine 
• 116360-41-9 N-<(trimethylstannyl)methyl>benzaldimine 
• 885613-08-1 2-methoxy-3-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 147410-41-1 N-(tert-butoxycarbonyl)-2-hydroxy-3-phenylpyrrolidine 
• 7699-79-8 benzhydrylidene-benzyl-amine 
• 100-46-9 benzylamine 
• 3555-71-3 N-benzyl-N-chloromethylamine 
• 103-67-3 benzyl-methyl-amine 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Relevant academic research and scientific papers

A practical one-pot synthesis of trans-4,5-disubstituted 2-pyrrolidinones and the related pyrrolidines

A practical and general method for the stereoselective synthesis of trans-4,5-disubstituted 2-pyrrolidinones was developed. Hydride reduction of these pyrrolidinones gave the corresponding pyrrolidines.

Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates

2-Arylpyrrolidines occur frequently in bioactive compounds, and thus, methods to access them from readily available reagents are valuable. We report a copper-catalyzed intermolecular carboamination of vinylarenes with potassium N-carbamoyl-β-aminoethyltrifluoroborates. The reaction occurs with terminal, 1,2-disubstituted, and 1,1-disubstituted vinylarenes bearing a number of functional groups. 1,3-Dienes are also good substrates, and their reactions give 2-vinylpyrrolidines. Radical clock mechanistic experiments are consistent with the presence of carbon radical intermediates and do not support participation of carbocations.

Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation

Exposure of N-chloroamines to KOtBu or LDA, in the presence of PMDETA or HMPA, provides 2-azaallyl anions capable of π4s + π2s cycloaddition reactions with a range of olefins. Good yields were achieved with stabilised systems, however, they were more modest when accessing semi-stabilised 2-azaallyl anions. By modifying the reaction conditions, one-pot dehydrochlorination/allylation can also be achieved with a range of N-chloroamines.

Stereoselective synthesis of trans-2,3-disubstituted pyrrolidines via addition to N-acyliminium ions

An efficient and stereoselective synthesis of trans-2,3-disubstituted pyrrolidines is described. The intermolecular alkylation of racemic N-acyliminium ions generated in situ from the corresponding 3-substituted lactams proceeds stereoselectively and in h

Generation of 2-azaallyl anions by the transmetalation of N-(trialkylstannyl)methanimines. Pyrrolidine synthesis by [3 + 2] cycloadditions with alkenes

Treatment of N-(trimethylstannyl)methanimines or N-(tri-n-butylstannyl)methanimines with methyllithium or n-butyllithium, respectively, affords 2-azaallyl anions by tin-lithium exchange. These anions undergo intermolecular or intramolecular [π4s + π2s] cycloadditions with alkenes and alkynes to generate pyrrolidines or pyrrolines after quenching with water or other electrophiles. The tin-lithium exchange method allows unstabilized 2-azaallyl anions to be generated for the first time. The lifetime of the anions is limited by a competing intermolecular side reaction. Therefore, relatively reactive alkenes and alkynes must be used, such as stilbene, styrenes, enynes, diphenylacetylene, vinyl sulfides, vinyl selenides, and vinyl silanes. The latter three types of anionophiles afford functionalized cycloadducts which may be transformed into more useful pyrrolidines by reduction, elimination, or oxidation. A synthesis of the alkaloid (±)-mesembrane was accomplished using an intramolecular 2-azaallyl anion cycloaddition.

TRANSMETALLATION OF N-(TRIALKYLSTANNYL)METHYLIMINES. A NEW METHOD FOR THE GENERATION AND CYCLOADDITION OF 2-AZAALLYL ANIONS.

Transmetallation of imines 1 at -78 deg C with RLi provided 2-azaallyl anions 2, which readily undergo cycloaddition with olefinic anionophiles, providing pyrrolidines.Of particular note is the generation of unstabilized 2-azaallyl anions for the first ti

Synthetic Versatility of N(Silylmethyl)imines: Water-Induced Generation of N-Protonated Azomethine Ylides of Nonstabilized Type and Fluoride-Induced Generation of 2-Azallyl Anions

N-(Silylmethyl)imines generate N-protonated azomethine ylides of nonstabilized type when treated with water in HMPA, which undergo stereospecific and regioselective cycloadditions with electron-poor olefins affording N-unsubstituted pyrrolidines.On the other hand, fluoride-induced desilylation of the imines leads to 2-azallyl anions which are found to be synthetic equivalents of aminomethyl anion in the Michael additions with electron-poor olefins and nucleophilic additions with carbonyl compounds.