129748-75-0

Upstream product

• 4375-14-8 octahydro-1H-indole 
• 98-59-9 p-toluenesulfonyl chloride 
• 389079-71-4 N-(2-(cyclohex-1-en-1-yl)ethyl)-4-methylbenzenesulfonamide 
• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 57981-18-7 N-cyclohex-2-enyl-4-methyl-benzenesulfonamide 
• 129748-76-1 (±)-N-(2-bromoethyl)-N-(cyclohex-2-en-1-yl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Calcium(II)-Catalyzed Intra- and Intermolecular Hydroamidation of Unactivated Alkenes in Hexafluoroisopropanol

A combination of a calcium(II) triflimide salt and hexafluoroisopropanol (HFIP) was found to be a highly efficient promoter system for the intra- and intermolecular hydroamidation of unactivated alkenes. Unlike other methods, a vast array of functional groups is tolerated at the nitrogen and alkene moieties. The reaction produces the corresponding nitrogen-containing compounds in excellent yields and good diastereoselectivities. The use of HFIP as solvent proved crucial for the proper carrying out of this transformation. Its role, as well as that of calcium and its NTf2 ligand, was rationalized by DFT computations. These calculations show how the [(NTf2)Ca(HFIP)n]+ complex can activate the amide via a basic site of the NTf2 ligand and the alkene with one acidic HFIP proton. The acidity of HFIP is exacerbated by the coordination to the calcium center, the more so as n increases.

Anti-markovnikov hydroamination of alkenes catalyzed by an organic photoredox system

Herein we report a metal-free method for the direct anti-Markovnikov hydroamination of unsaturated amines. Irradiation of the amine substrates with visible light in the presence of catalytic quantities of easily synthesized 9-mesityl-10-methylacridinium t

Studies concerning the electrophilic amino-alkene cyclisation for the synthesis of bicyclic amines

The bromination of a series of cyclohexenyl substituted secondary amines 1a-i has been investigated using Br2, PHT and NBS. In the case of Br2 and NBS the secondary amines preferentially undergo N-bromination. In contrast, PHT cleanly affords the products of alkene dibromination. In the case of Br2 the N-bromo species then give the products of alkene dibromination, albeit less efficiently. On subsequent treatment with K2CO3 these dibromides form the corresponding hexahydroindoles 2a-h and octahydroquinoline 2i. The presence of an N-substituent bearing a stereogenic centre (1h and 1i) was studied and the products 2h and 2i were isolated with no diastereoselectivity. When NBS was used a novel cyclisation, forming bromo-substituted octahydroindoles 9a,b and d, was observed. In relation to this sequence it was shown that these products were not intermediates in the former Br2/PHT processes and that the reaction only proceeded in the presence of the succinimide by-product of N-bromination.

VERSATILE METHODS OF SYNTHESIS OF 5 TO 8-MEMBERED RING N-HETEROCYCLES VIA INTRAMOLECULAR CYCLOADDITIONS OF ALLYLAMINES

N-Tosylallylamines or homoallylamines were monoalkylated with dibromoalkanes to produce bromoalkylamines 3 or 7.The latter were converted to unsaturated nitro derivatives which, via nitrile oxides, underwent intramolecular cycloaddition to form hetero rin