96039-76-8

Upstream product

• 57466-29-2 cis-2-cyclohexene-1,4-diol monoacetate 
• 78776-45-1 cis-2-cyclohexenyl-1,4-diacetate 
• 53762-85-9 (1S,4R)-Cyclohex-2-ene-1,4-diol 
• 64-19-7 acetic acid 
• 1165952-91-9 cyclohexa-1,3-diene 

Downstream Products

• 120568-77-6 Acetic acid (1S,4S)-4-[but-3-enyl-(toluene-4-sulfonyl)-amino]-cyclohex-2-enyl ester 
• 18683-91-5 ambroxol 
• 46727-91-7 N-(o-aminobenzyl)-trans-4-aminocyclohexanol 
• 120568-88-9 (3S,3aR,7aR)-1-(Toluene-4-sulfonyl)-3-vinyl-2,3,3a,6,7,7a-hexahydro-1H-indole 
• 120568-78-7 (4aR,8aR)-4-Methylene-1-(toluene-4-sulfonyl)-1,2,3,4,4a,7,8,8a-octahydro-quinoline 
• 120568-79-8 Acetic acid (1S,4S)-4-[((Z)-but-2-enyl)-(toluene-4-sulfonyl)-amino]-cyclohex-2-enyl ester 

Relevant academic research and scientific papers

Palladium-Hydroquinone Catalysed Electrochemical 1,4-Oxidation of Conjugated Dienes

The mediator system palladium(II)-hydroquinone was shown to catalyse the anodic oxidation of cyclohexa-1,3-diene in acetic acid to produce selectively either trans- or cis-1,4-diacetoxycyclohex-2-ene (1) depending on the conditions.

Pyrrolizidine alkaloids by intramolecular palladium-catalysed allylic alkylation: Synthesis of (±)-isoretronecanol

An efficient and stereoconvergent approach to 3-substituted hexahydroindol-2-one derivatives by palladium-catalysed intramolecular allylic alkylation has been developed. Subsequently, the straightforward conversion of the hexahydroindol-2-one 7d into the alkaloid (±)-isoretronecanol has been performed. The synthesis entails 11 steps starting from 1,3-cyclohexadiene, affording the final target in a 29% overall yield. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Palladium-catalysed enantiodivergent synthesis of cis- and trans-4-aminocyclohex-2-enols

Enantiomerically pure cis- and trans-4-aminocyclohex-2-enols are prepared from cyclohexa-1,3-diene via (-)-cis-(1R,4S)-4-acetoxycyclohex-2-enol (-)-2a using palladium(0) chemistry. Benzylamine and diethylamine are tested in the Pd0-catalysed allylic amination reactions. Since acetate is too slow as a leaving group and gave considerable amounts of side products, a number of leaving groups have been investigated. Of these phosphinate and 2,4-dichlorobenzoate are excellent leaving groups and result in efficient and highly stereoselective reactions; chloride as allylic leaving group also gives good results. By variation of the leaving group and proper choice of the protecting group it is possible to synthesise all four stereoisomers of 4-aminocyclohex-2-enol in good yield and high enantiomeric excess.

Aerobic Palladium-catalysed 1,4-cis-Diacetoxylation and 1,4-cis-Chloroacetoxylation of Cyclohexa-1,3-diene using a Tetrakis(methoxyhydroquinone)porphyrin

The use of Co(tetraphenylporphyrins), carrying methoxy substituents in the meso-phenyl groups, in aerobic, quinone-free palladium-catalysed 1,4-oxidations of cyclohexa-1,3-diene provides an entry to cis-disubstituted products, until now inaccessible by ae