87562-50-3

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 126-98-7 methacrylonitrile 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 78-82-0 Isobutyronitrile 
• 260352-12-3 (E)-5-(4-chlorophenyl)-2,2-diphenylpent-4-enal 
• 1431561-40-8 (1E, 4E)-2,2-dimethyl-5-phenylpent-4-enal oxime 

Downstream Products

• 1426431-63-1 (E)-2,2-dimethyl-5-phenylpent-4-enylamine-N,N-D₂ 
• 1206670-48-5 2-benzyl-4,4-dimethyl-1-(4-methylbenzenesulfonyl)pyrrolidine 
• 260352-12-3 (E)-5-(4-chlorophenyl)-2,2-diphenylpent-4-enal 
• 1583276-76-9 (E)-4,4-dimethyl-1-phenyldeca-1,9-dien-5-ol 
• 1583276-77-0 (E)-4,4-dimethyl-1-phenyldeca-1,9-dien-5-one 
• 1583276-42-9 (1Z,4E)-1-(4-methoxyphenyl)-2,2-dimethyl-5-phenylpent-4-en-1-one oxime 
• 1583276-43-0 (1Z,4E)-2,2-dimethyl-5-phenyl-1-(4-(trifluoromethyl)phenyl)pent-4-en-1-one oxime 
• 1583276-44-1 (1Z,4E)-2,2-dimethyl-1-(naphthalen-2-yl)-5-phenylpent-4-en-1-one oxime 
• 1583276-46-3 (1Z,4E)-2,2-dimethyl-5-phenyl-1-(thiophen-2-yl)pent-4-en-1-one oxime 
• 1583276-41-8 (2E,5E)-3,3-dimethyl-6-phenylhex-5-en-2-one oxime 
• 1583276-60-1 (1E,5E)-4,4-dimethyl-1-phenyldeca-1,9-dien-5-one oxime 
• 1431561-40-8 (1E, 4E)-2,2-dimethyl-5-phenylpent-4-enal oxime 
• 1583276-18-9 2-benzyl-4, 4-dimethyl-5-phenyl-3, 4-dihydro-2H-pyrrole 1-oxide 
• 1583276-19-0 2-benzyl-5-(4-methoxyphenyl)-4,4-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide 

Relevant academic research and scientific papers

Base-catalysed asymmetric hydroamination/cyclisation of aminoalkenes utilising a dimeric chiral diamidobinaphthyl dilithium salt

A dimeric proline derived diamidobinaphthyl dilithium salt represents the first example of a chiral main group metal based catalyst for asymmetric hydroamination/cyclisation reactions of aminoalkenes. The Royal Society of Chemistry 2006.

C1-symmetric β-Diketiminatoiron(II) Complexes for Hydroamination of Primary Alkenylamines

The synthesis and solid-state characterization of an array of well-defined low-coordinate C1-symmetric β-diketiminatoiron(II) alkyl complexes B3–B6 featuring steric and electronic variations on one of the N-aryl substituen

Niobium-Catalyzed Intramolecular Addition of O-H and N-H Bonds to Alkenes: A Tool for Hydrofunctionalization

A convenient, versatile, and easy to handle intramolecular hydrofunctionalization of alkenes (C-O and C-N bonds formation) is reported using a novel niobium-based catalytic system. This atom economic and eco-friendly methodology provides an additional synthetic tool for the straightforward formation of valuable building blocks enabling molecular complexity. Various pyran, furan, pyrrolidine, piperidine, lactone, and lactam derivatives as well as spirocyclic compounds are produced in high yields and selectivities.

Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones

A method based on hydroamination mediated by inorganic base was developed for the synthesis of cyclic nitrones from alkenyl oximes. DFT calculations of the reaction pathway suggested that this hydroamination could proceed through an unprecedented nucleophilic amination of the unactivated alkene by the oxime nitrogen atom. The transition state of this reaction is stabilized by an ionic interaction between a metal cation such as K+ and the oxime oxygen and negatively charged alkene moiety. Basic ring building: A method for the synthesis of cyclic nitrones by using alkenyl oximes was developed based on hydroamination mediated by an inorganic base. DFT calculations for the reaction pathway suggested that this hydroamination could proceed through nucleophilic amination of the unactivated alkene by the oxime nitrogen atom, with the transition state stabilized by ionic interaction with a metal cation such as K+. Copyright

Substrate structural effects in yttrium(III)-catalyzed hydroamination/ cyclizations of 1,2-disubstituted and 1,1,2-trisubstituted aminoalkenes terminated by 2-(phenyl) and 2-(2-heteroarenyl) groups

A series of 2-phenyl- and 2-(2-heteroarenyl)-bearing amines possessing 1,2-disubstituted and 1,1,2-trisubststuted alkenes have been evaluated in intramolecular hydroaminations catalyzed by Y[N(TMS)(1. Aminoalkenes possessing a terminal 2-(5-trimethylsilyl)thienyl group exhibited substantially enhanced reactivity compared to their 2-(phenyl)-containing counterparts. Cyclization efficiencies imparted by the 2-[(5-trimethylsilyl)furanyl] substituent were comparable or only slightly better than those obtained with the simple the 2-(phenyl) group. Georg Thieme Verlag Stuttgart · New York.

PhI(OAc)2-mediated iminobromination for synthesis of bromomethyl cyclic imines starting from alkenyl carbonitriles and Grignard reagents

PhI(OAc)2-mediated iminobromination was developed starting from alkenyl carbonitriles and Grignard reagents. The present transformation is carried out by a sequence of nucleophilic addition of Grignard reagents to alkenyl carbonitriles to form

3,3′-Bis(trisarylsilyl)-substituted binaphtholate rare earth metal catalysts for asymmetric hydroamination

Chiral 3,3′-bis(trisarylsilyl)-substituted binaphtholate rare earth metal complexes (R)-[Ln{Binol-SiAr3}(o-C6H 4CH2NMe2)(Me2NCH2Ph)] (Ln = Sc, Lu, Y; Binol-SiAr3 = 3,3′-bis(trisarylsilyl)-2,2′- dihydroxy-1,1′-binaphthyl; Ar = Ph (2-Ln), 3,5-xylyl (3-Ln)) and (R)-[La{Binol-Si(3,5-xylyl)3}{E(SiMe3)2}(THF) 2] (E = CH (4a), N (4b)) are accessible via facile arene, alkane, and amine elimination. They are efficient catalysts for the asymmetric hydroamination/cyclization of aminoalkenes, giving TOF of up to 840 h -1 at 25 °C for 2,2-diphenyl-pent-4-enylamine (5c) using (R)-2-Y. Enantioselectivities of up to 95% ee were achieved in the cyclization of 5c with (R)-2-Sc. The reactions show apparently zero-order rate dependence on substrate concentration and first-order rate dependence on catalyst concentration, but rates depend on total amine concentrations. Activation parameters for the cyclization of pent-4-enylamine using (R)-2-Y (ΔH(S)? = 57.4-(0.8) kJ mol-1 and ΔS(S)? = -102(3) J K-1 mol-1; ΔH(R)? = 61.5(0.7) kJ mol-1 and ΔS(R)? = -103(3) J K-1 mol -1) indicate a highly organized transition state. The binaphtholate catalysts were also applied to the kinetic resolution of chiral α-substituted aminoalkenes with resolution factors f of up to 19. The 2,5-disubstituted aminopentenes were formed in 7:1 to ≥50:1 trans diastereoselectivity, depending on the size of the α-substituent of the aminoalkene. Rate studies with (S)-1-phenyl-pent-4-enylamine ((S)-15e) gave the activation parameters for the matching (ΔH? = 52.2(2.8) kJ mol -1, ΔS? = -127(8) J K-1 mol-1 using (S)-2-Y) and mismatching (ΔH? = 57.7(1.3) kJ mol -1, ΔS? = -126(4) J K-1 mol-1 using (R)-2-Y) substrate/catalyst combination. The absolute configuration of the Mosher amide of (2S)-2-methyl-4,4-diphenyl-pyrrolidine and (2R)-methyl-(5S)- phenyl-pyrrolidinium chloride, prepared from (S)-15e, were determined by crystallographic analysis. Catalyst (R)-4a showed activity in the anti-Markovnikov addition of n-propylamine to styrene.

Indium(I) iodide promoted highly selective 1,2-addition of allyl and benzyl groups to α,β-unsaturated nitriles under sonication: A new synthesis of conjugated imines

Allyl and benzyl bromides react with α,β-unsaturated nitriles in the presence of indium(I) iodide under sonication to produce the corresponding allylated and benzylated conjugated imines involving exclusive addition of the allyl/benzyl group to the C≡N moiety.