58170-50-6

Upstream product

• 591-80-0 pent-4-enoic acid 
• 100-46-9 benzylamine 
• 39716-58-0 pent-4-enoyl chloride 
• 1968-40-7 ethyl 4-pentenoate 

Downstream Products

• 42856-59-7 5-hydroxy-N-(phenylmethyl)-pentanamide 
• 112146-13-1 4-hydroxy-4-methyl-N-(phenylmethyl)-butanamide 
• 54436-58-7 N-benzylpent-4-en-1-amine 
• 171017-16-6 N-benzyl-N-tert-butoxycarbonyl-4-pentenamide 
• 470678-25-2 benzyl-pent-4-enoyl-carbamic acid benzyl ester 
• 632326-42-2 N-[1,1-bis(2-methylallyl)pent-4-enyl]benzylamine 
• 171017-17-7 N-benzyl-N-tert-butoxycarbonyl-4-oxo-butanamide 
• 171017-25-7 N-Benzyl-4-[4-methyl-5-oxo-1,5-dihydro-pyrrol-(2E)-ylidene]-butyramide 
• 215106-54-0 N-Benzyl-4-[4-methyl-5-oxo-1,5-dihydro-pyrrol-(2Z)-ylidene]-butyramide 
• 171017-31-5 5-[4-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-but-(Z)-ylidene]-3-methyl-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 171017-24-6 5-[4-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-but-(E)-ylidene]-3-methyl-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 6560-75-4 1-benzyl-3-methylpiperidine 
• 20422-13-3 1-benzylazepane 
• 37672-46-1 3-methyl-1-(phenylmethyl)-2-piperidinone 

Relevant academic research and scientific papers

Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization-Hydroboration of Unactivated Alkenes

A tungsten-catalyzed hydroboration of unactivated alkenes at distal C(sp3)-H bonds aided by native directing groups is described herein. The method is characterized by its simplicity, exquisite regio- and chemoselectivity, and wide substrate scope, offering a complementary site-selectivity pattern to other metal-catalyzed borylation reactions and chain-walking protocols.

Diethylzinc-Mediated Radical 1,2-Addition of Alkenes and Alkynes

A novel diethylzinc-mediated radical 1,2-addition of perfluoroalkyl iodides to unactivated alkenes and alkynes is presented, which demonstrates a novel way to generate an ethyl difluoroacetate radical. This method is highly efficient and gives full conversions of the substrates, high yields of the products, and negligible byproducts and requires no column chromatography purifications. The mild conditions enable this protocol to exhibit excellent functional group compatibility.

Practical Synthesis of Halogenated N-Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes

A general and efficient intramolecular halo-amination of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N-heterocycles, including three-, five-, and six-membered N-heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach.

Iridium-Catalyzed Aerobic α,β-Dehydrogenation of γ,δ-Unsaturated Amides and Acids: Activation of Both α- And β-C-H bonds through an Allyl-Iridium Intermediate

Direct aerobic α,β-dehydrogenation of γ, δ-unsaturated amides and acids using a simple iridium/copper relay catalysis system is described. We developed a new strategy that overcomes the challenging issue associated with the low α-acidity of amides and acids. Instead of α-C-H metalation, this reaction proceeds by β-C-H activation, which results in enhanced α-acidity. Conjugated dienamides and dienoic acids were synthesized in excellent yield with this reaction, which uses a simple reaction protocol. Mechanistic experiments suggest a catalyst resting state mechanism in which both α-C-H and β-C-H cleavage is accelerated.

Catalytic hydrotrifluoromethylation of unactivated alkenes

A visible-light-mediated hydrotrifluoromethylation of unactivated alkenes that uses the Umemoto reagent as the CF3 source and MeOH as the reductant is disclosed. This effective transformation operates at room temperature in the presence of 5 mol % Ru(bpy)3Cl2; the process is characterized by its operational simplicity and functional group tolerance.

Reductive hydroxyalkylation/alkylation of amines with lactones/esters

We have developed a one-pot method for the direct intermolecular reductive hydroxyalkylation or alkylation of amines using lactones or esters as the hydroxyalkylating/alkylating reagents. The method is based on the in situ amidation of lactones/esters with DIBAL-H-amine complex (for primary amines) or DIBAL-H-amine hydrochloride salt complex (for secondary amines), followed by reduction of the amides with an excess of DIBAL-H. Different from the reduction of Weinreb amides with DIBAL-H where aldehydes are formed, the reduction of the in situ formed Weinreb amides yielded amines. Moreover, this method is not limited to Weinreb amides, instead, it also works for other amides in general. A plausible mechanism is suggested to account for the outcome of the reactions.

Enantioselective Synthesis of Cyclic Secondary Amines through Mo-Catalyzed Asymmetric Ring-Closing Metathesis (ARCM)

(Equation Presented) Carboyclic amines are synthesized efficiently in up to 93% ee by asymmetric ring-closing metathesis (ARCM) with 2-5 mol % chiral Mo complexes. An example is provided where the catalyst is prepared in situ (catalyst isolation not neede

Tandem cyclisations of amidyl radicals derived from O-acyl hydroxamic acid derivatives

Amidyl radicals generated from tributylstannane mediated homolysis of O- acyl hydroxamic acid derivatives 5a-b undergo tandem cyclisations to give pyrrolizidinones 6a-c and indolizidinones 7a-b respectively while 5c-d undergo monocyclisation to give β-lac

Synthesis of azaspiro[4.5]decane systems by oxidative cyclization of olefinic precursors

The synthesis of 6-benzyloxycarbonyl-1-oxa-6-azaspiro[4.5]decan-2-one (17) and 6-benzyloxycarbonyl-1,6-diazaspiro[4.5]decan-2-one (18) from the D,L-pipecolic acid derivative 10, is described. The synthesis of (±)-6- benzyl-3-methyl-1,6-diazaspiro[4.5]dec-3-ene-2,7-dione (29), the spiro structural unit of (±)-pandamarine (8) has been achieved by oxidative cyclization of the (Z) and (E) isomers of 5-(N-benzyl-4- carboxamidobutylidene)-3-methyl-3-pyrrolin-2-one (25) and (26). The stereoselectivity obtained in the intramolecular cyclization process has also been discussed.

Synthesis of α,β-Unsaturated Spirolactams by Intramolecular Cyclization of Endocyclic N-Acyliminium Ions

The synthesis of (+/-)-6-benzyl-3-methyl-3-en-1,6-diazaspirodecane-2,7-dione (18), the spiro moiety of (+/-)-pandamarine has been achieved by oxidative cyclization of the (Z) and (E) isomers of 5-(N-benzyl-4-carboxamido-butylidene)-3-methyl-3-en-pyrrolin-2-one (15a) and (15b).The stereoselectivity exhibited in the intramolecular cyclization by both butylidene precursors has also been discussed.