84010-75-3

Upstream product

• 132283-72-8 (1S,1'R)-2-(2-hydroxy-1-phenylethyl)-1-phenethyl-1,2,3,4-tetrahydroisoquinoline 
• 90482-02-3 (S)-valinol-tert-butyl ether formamidine of 1,2,3,4 tetrahydro-isoquinoline 
• 103-63-9 1-phenyl-2-bromoethane 
• 84010-65-1 [1-(3,4-Dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-((1S,2S)-2-phenyl-2-trimethylsilanyloxy-1-trimethylsilanyloxymethyl-ethyl)-amine 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 3230-65-7 3,4-dihydroisoquinoline 
• 78317-83-6 2-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 81045-39-8 5,8-dibromoisoquinoline 
• 1337924-60-3 C₂₄H₂₀N₂O 
• 1337924-99-8 C₂₄H₂₄N₂O 
• 536-74-3 phenylacetylene 
• 132283-66-0 (R)-3-Phenyl-2,3,6,10b-tetrahydro-5H-oxazolo[2,3-a]isoquinoline 
• 90878-19-6 phenethylmagnesium chloride 

Relevant academic research and scientific papers

Catalytic addition of alkenylzirconocene chloride to 3,4-dihydroisoquinoline and its enantioselective reaction

The addition of alkenylzirconocene chloride to 3,4-dihydroisoquinoline in the presence of a stoichiometric amount of acylating agent such as (Boc)2O or ClCOOC2H5 was carried out in the presence of a catalytic amount of Cu(

CuII/TEMPO-Catalyzed Enantioselective C(sp3)–H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation

A novel strategy for asymmetric Shono-type oxidative cross-coupling has been developed by merging copper catalysis and electrochemistry, affording C1-alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co-catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported.

Asymmetric Aerobic Oxidative Cross-Coupling of Tetrahydroisoquinolines with Alkynes

An efficient asymmetric aerobic oxidation of tetrahydroisoquinolines with terminal alkynes was realized under mild reaction conditions using O2 as the sole oxidant. A chiral N,N′-dioxide/zinc(II)/iron(II) bimetallic cooperative catalytic system

Reissert-like alkenylation of azaaromatic compounds with alkenylzirconocene chloride complexes

Reissert-like alkenylation of azaaromatic compounds by the use of alkenylzirconocene chloride as a nucleophile was carried out in the presence of a stoichiometric amount of ClCO2Et. The regioselectivity of the nucleophilic attack depends on reacting heterocycles, solvent, and the presence of copper catalyst. Thus, the reaction of quinoline derivatives with alkenylzirconocene chloride in MeNO2 proceeded in a preferential 1,2-addition manner to give N-ethoxycarbonyl-2-alkenyl-1,2-dihydroquinolines, and the reaction of pyridine in CH2Cl2 under Cu(I)-catalyzed conditions proceeded in a 1,4-addition manner to give N-ethoxycarbonyl-4-alkenyl-1,4-dihydropyridine. The alkenylation of 3,4- dihydroisoquinoline with alkenylzirconocene chloride was also carried out in an enantioselective manner under Cu(I)/chiral Box-catalyzed conditions to give alkenylated tetrahydroisoquinoline compound (75%ee).

Catalytic asymmetric alkynylation of C1-substituted C,N-cyclic azomethine imines by CuI/chiral bronsted acid co-catalyst

It all adds up: The title reaction was developed for the synthesis of chiral tetrahydroisoquinoline derivatives with a tetrasubstituted carbon center at the C1-position (see scheme, Bz=benzoyl, pybox=2,6-bis(2-oxazolinyl)pyridine) . The reaction was facilitated effectively by the co-catalyst system composed of copper(I)/Ph-pybox and an axially chiral dicarboxylic acid.

Asymmetric addition of nucleophiles to C-1 position of isoquinolines using (S)-alanine derivatives as chiral auxiliaries

5,8-Dibromoisoquinoline derivatives were allowed to react with a nucleophile (silyl enol ether or allyltributyltin) in the presence of an acyl chloride derived from (S)-alanine to afford the 1,2-addition products in good chemical yields and high stereoselectivity. The bromo groups were readily removed by a reduction process in which the double bond at C3-C4 was also reduced. Thus the reaction system provided a general method to synthesize asymmetric 1-substituted tetrahydroisoquinolines. In order to determine the absolute configuration of the reaction product, (-)-homolaudanosine was synthesized in an enantiopure form. The stereoselectivity was rationally understood from the conformation of intermediary N-acylated isoquinolinium salts.

ENANTIOSELECTIVE ALKYLATION OF α-AMINO CARBANIONSTHE SYNTHESIS OF (S)-1-ALKYL-1,2,3,4 TETRAHYDROISOQUINOLINES

A series of chiral amino alcohols transformed into the formamidine derivative of 1,2,3,4-tetrahydroisoquinolines were evaluated as chiral dipole-stabilized anions.Alkylation with alkyl halides provided the 1-alkyl-1,2,3,4-tetrahydroisoquinolines in both e