66120-27-2

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 157634-01-0 N-benzylpiperidine-2-carbaldehyde 
• 4783-65-7 N-benzyl-2-piperidinone 
• 3536-96-7 vinylmagnesium chloride 
• 100-39-0 benzyl bromide 
• 1415356-90-9 (E)-7-bromohept-2-en-1-yl isobutyl carbonate 
• 113558-64-8 (E)-7-bromohept-2-en-1-ol 
• 111710-77-1 ethyl 7-bromo-2-(E)-heptenoate 
• 1191-30-6 5-bromopentanal 
• 14660-52-7 ethyl 5-bromovalerate 
• 100-52-7 benzaldehyde 
• 1268717-79-8 (Z)-6-(N-benzylamino)-2-heptenol 
• 100-46-9 benzylamine 
• 50983-76-1 hepta-5,6-dien-1-yl 4-methylbenzenesulfonate 

Downstream Products

• 76707-69-2 1-benzyl-2-vinylpiperidine N-oxide 
• 135311-14-7 hexahydroazec-5-en-2-one 
• 177665-11-1 9-(benzylamino)-2-methyl-2-methoxynon-4-enoic acid lactam 
• 849937-10-6 2-(tert-butyldimethylsilyloxy)-2-phenyl-1-(2-vinylpiperidin-1-yl)ethan-1-one 
• 849937-14-0 (E)-3-(tert-butyldimethylsilyloxy)-1,2,3,4,7,8,9,10-octahydro-3-phenylazecine 
• 849937-12-8 (E)-3-(tert-butyldimethylsilyloxy)-3,4,7,8,9,10-hexahydro-3-phenylazecin-2(1H)-one 
• 37848-70-7 2-vinylpiperidine 
• 439928-99-1 1,2,3,6,7,8,9,9a-octahydro-3-phenyl-2H-quinolizin-3-ol 
• 76707-74-9 1-benzyloxy-2-vinylpiperidine 
• 76707-73-8 2-benzyl-7-vinylhexahydro-1,2-oxazepine 
• 914402-87-2 C₂₃H₂₇NO₂S 
• 1184350-77-3 C₂₀H₂₃N 

Relevant academic research and scientific papers

Transition-Metal-Free Reductive Functionalization of Tertiary Carboxamides and Lactams for α-Branched Amine Synthesis

A new method for the synthesis of α-branched amines by reductive functionalization of tertiary carboxamides and lactams is described. The process relies on the efficient and controlled reduction of tertiary amides by a sodium hydride/sodium iodide composite, in situ treatment of the resulting anionic hemiaminal with trimethylsilyl chloride and subsequent coupling with nucleophilic reagents including Grignard reagents and tetrabutylammonium cyanide. The new method exhibits broad functional-group compatibility, operates under transition-metal-free reaction conditions, and is suitable for various synthetic applications on both sub-millimole and on multigram scales.

Enantioselective synthesis of N-heterocycles via intramolecular Pd(0)-catalysed allylic amination

An efficient and stereoselective synthesis of pyrrolidine-, piperidine-, and azepane-type N-heterocycles is described by the intramolecular Pd(0)-catalysed cyclisation of amino allylic carbonates. The use of chiral ligands gave the corresponding heterocyclic derivatives having er values that were from moderate to good.

Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines

A 1:1 mixture of (1)AuCl [1 = P(t-Bu)2o-biphenyl] and AgSbF 6 catalyzes the intramolecular amination of allylic alcohols with alkylamines to form substituted pyrrolidine and piperidine derivatives. Gold(I)-catalyzed cyclization of (R,Z)-8-(N-benzylamino)-3-octen-2-ol (96% ee, 95% de) led to isolation of (R,E)-1-benzyl-2-(1-propenyl)piperidine in 99% yield with 96% ee, consistent with the net syn addition of the amine relative to the departing hydroxyl group.

Copper-catalyzed intramolecular hydroamination of allenylamines to 3-pyrrolines or 2-alkenylpyrrolidines

Copper salts, such as CuCl, CuI, CuCl2 and Cu(OTf)2, were used to catalyze the intramolecular hydroamination of allenylamines to provide the corresponding 3-pyrrolines or 2-alkenylpyrrolidines.

Synthesis of functionalised azecine and azonine derivatives via an enolate assisted aza Claisen rearrangement

This paper describes the synthesis of functionalised azecine and azonine derivatives incorporating the adrenaline motif. In a key step, an enolate assisted aza Claisen rearrangement was employed to interconvert from 6- and 5-membered heterocycles to their corresponding 10- and 9-membered lactams.

Synthesis of α-substituted allylic amines via a modified Bruylants reaction

equation presented Silver tetrafluoroborate, used as an iminium ion promoter from α-amino nitriles, is an efficient additive in the Bruylants reaction involving vinylic Grignards. Improved yields of allylic amines were obtained when the starting α-amino n

Palladium-catalyzed reactions of N-allylbenzotriazoles with amines: Intramolecular allylamination routes to 2-vinylpyrrolidines and 2- vinylpiperidines

Reactions of allylbenzotriazole (4a-d) with 1-bromo-3-chloropropane, 1- bromo-2-methyl-3-chloropropane, epibromohydrin (8), and 1-bromo-4- chlorobutane afforded the corresponding α-substituted allylbenzotriazoles (5a-d, 9, and 16a,b), which with primary amines in one-pot sequences produce 2-vinylpyrrolidines (7a-i), 2-ethylpyrrole (13), and 2-vinylpiperidines (18a- c) in good yields under mild conditions.

Photochemical reaction between tertiary allylic amines and chromium carbene complexes: Synthesis of lactams via a zwitterion aza cope rearrangement

Photolysis of chromium carbene complexes in the presence of tertiary allylic amines resulted in a zwitterionic aza Cope rearrangement to produce unsaturated lactams in fair yield.

CYCLISATION D'AMINES γ ET δ-ALLENIQUES. SYNTHESE D'ALCENYL-2 PYRROLIDINES ET D'ALCENYL-2- PIPERIDINES

The entitled heterocyclic compounds can be obtained with good yields and exclusively with E configuration by the respective cyclisation of secondary γ-allenic and δ-allenic amines promoted by silver nitrate or by mercuric chloride.In the second case, the