59816-88-5

Upstream product

• 61436-87-1 2-allyl-benzamide 
• 2042-37-7 o-cyanobromobenzene 
• 61463-61-4 2-allylbenzonitrile 
• 62708-42-3 o-allylbenzaldehyde 
• 160350-20-9 2-allylbenzaldehyde oxime 

Downstream Products

• 1043416-23-4 2-allyl-benzylamine*HOTf 
• 1085337-39-8 N-trityl-L-serine (o-allylbenzyl)amide 
• 1085337-40-1 N-trityl-D-serine (o-allylbenzyl)amide 
• 1103771-45-4 N-benzyloxycarbonyl-2-allylbenzyl amine 
• 15547-43-0 3-(S)-methyl-1,2,3,4-tetrahydroisoquinoline 
• 179893-97-1 (3R)-3-methyl-1,2,3,4-tetrahydroisoquinoline 
• 168902-85-0 cis-1-amino-2-methylindane 
• 168902-85-0 trans-1-amino-2-methylindane 

Relevant academic research and scientific papers

Palladium-catalyzed selective aminoamidation and aminocyanation of alkenes using isonitrile as amide and cyanide sources

A mild and efficient palladium-catalyzed intermolecular aminoamidation and aminocyanation reaction of alkenes with a broad substrate scope has been developed. This cyclization process provides a valuable synthetic tool for obtaining substituted indolines, tetrahydroisoquinolines and pyrrolidines in good to excellent yields. This journal is

One-pot Construction of Difluorinated Pyrrolizidine and Indolizidine Scaffolds via Copper-Catalyzed Radical Cascade Annulation

A convenient approach to the synthesis of diverse difluorinated nitrogen-containing polycycles via a copper-catalyzed radical cascade annulation of amine-containing olefins and ethyl bromodifluoroacetate was developed. Three new bonds, including a Csp3 ?CF2 and two C?N bonds, are forged simultaneously in this strategy. Through this strategy, a series of difluorinated pyrrolizidine and indolizidine derivatives have been conveniently synthesized in good yields. (Figure presented.).

Copper-Catalyzed Redox-Triggered Remote C-H Functionalization: Highly Selective Formation of C-CF3 and C-O Bonds

A Cu-catalyzed remote sp3 C-H/unactivated alkenes functionalization reaction for the concomitant construction of C-CF3 and C-O bonds was described. An 1,5-H radical transfer involving an sp3 C-H bond adjacent to a nitrogen atom and an α-CF3-alkyl radical intermediate derived from unactivated alkenes was observed and demonstrated to proceed via the radical process. C-CF3 formation/1,5-H radical shift/remote functionalization of sp3 C-H bond.

Enantioselective C-H bond functionalization triggered by radical trifluoromethylation of unactivated alkene

An asymmetric unactivated alkene/C-H bond difunctionalization reaction for the concomitant construction of C-CF3 and C-Obonds was realized by using a Cu/Bronsted acid cooperative catalytic system, thus providing facile access to valuable chiral

Intramolecular hydroamination of unbiased and functionalized primary aminoalkenes catalyzed by a rhodium aminophosphine complex

We report a rhodium catalyst that exhibits high reactivity for the hydroamination of primary aminoalkenes that are unbiased toward cyclization and that possess functional groups incompatible with more electrophilic hydroamination catalysts. The rhodium catalyst contains an unusual diaminophosphine ligand (L1) that binds to rhodium in a K3-P,O,P mode. The reactions catalyzed by this complex typically proceed at mild temperatures (room temperature to 70 °C) and occur with primary aminoalkenes lacking substituents on the alkyl chain that bias the system toward cyclization, with primary aminoalkenes containing chloride, ester, ether, enolizable ketone, nitrile, and unprotected alcohol functionality, and with primary aminoalkenes containing internal olefins. Mechanistic data imply that these reactions occur with a turnover-limiting step that is different from that of reactions catalyzed by late-transition-metal complexes of Pd, Pt, and Ir. This change in the turnover-limiting step and resulting high activity of the catalyst stem from favorable relative rates for protonolysis of the M-C bond to release the hydroamination product versus reversion of the aminoalkyl intermediate to regenerate the acyclic precursor. Probes of the origin of the reactivity of the rhodium complex of L1 imply that the aminophosphine groups lead to these favorable rates by effects beyond steric demands and simple electron donation to the metal center.

Ring-opening of aziridine-2-carboxamides with carbohydrate C1-O-nucleophiles. Stereoselective preparation of α- and β-O-glycosyl serine conjugates

The stereoselective formation of the α-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles is described. The process is tolerant to the native C2-NHAc group, can be modulated to provide either the α- or β-glycoside through judicious choice of solvent and metal counterion, and is amenable to other classes of O-glycosyl-Ser constructs such as the β-GlcNAc-Ser and α-Man-Ser linkages. This coupling reaction also led to the development of the o-allylbenzyl (ABn) moiety as a new C-terminus carboxyl protective group, which allows for the use of novel methods for N- and C-terminus extension of amino acids following carbohydrate conjugation. Copyright

Gold(I)-catalyzed intramolecular hydroamination of unactivated C=C bonds with alkyl ammonium salts

A mixture of (5)AuCl {5 = PCy2[2-(2,6-C6H 3(OMe)2)C6H4]} and AgOTf catalyzes the intramolecular hydroamination of unactivated C=C bonds with primary and secondary ammonium salts. The Royal

Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles

The dimethyltitanocene methylenation of N-acylamides derived from ortho-vinylanilines, ortho-allylaniline, and ortho-vinylbenzylamine provides the corresponding enamides, which upon exposure to the second generation Grubbs ruthenium catalyst give access to indoles, 1,4-dihydroquinolines, and 1,2-dihydroisoquinolines, respectively. This sequential protocol also allows the synthesis of dihydrobenzoazepines, although the ring-closing metathesis (RCM) step is complicated by the alkene isomerization processes. From certain substrates, the direct annulation is observed in the titanium-mediated step, which is likely to occur through an olefin metathesis-intramolecular olefination sequence.