125950-36-9

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 10458-14-7 (2R,5S)-menthone 
• 3391-87-5 l-menthone 
• 456-64-4 phenyl trifluoromethanesulfonamide 
• 412324-05-1 (3R,6S)-6-Isopropyl-3-methyl-cyclohex-1-enol 

Downstream Products

• 1106680-95-8 ethyl (2E,4E,6Z)-3-methyl-7-((3R,6S)-6-(1-methylethyl)-3-methyl-1-cyclohexen-1-yl)-2,4,6-octatrienoate 
• 1093863-44-5 (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoic acid 
• 1310340-32-9 (2E,4E,6Z)-7-[(3R,6S)-6-(1-methylethyl)-3-methylcyclohexen-1-yl]-3-methyl-2,4,6-octatrienoic acid 
• 1093863-59-2 ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6S)-6-isopropyl-3-methylcyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoate 
• 151671-72-6 (3R,6S)-1-iodo-6-isopropyl-3-methylcyclohex-1-ene 
• 125950-37-0 1-(1-ethoxyvinyl)-3(R)-methyl-6(S)-isopropylcyclohexene 

Relevant academic research and scientific papers

Ni(4?Tbustb)3: A robust 16-electron Ni(0) olefin complex for catalysis

Sixteen-electron Ni(0) complexes bearing trans-stilbene derivative ligands have been shown to display a high degree of stability toward oxidation in the solid state. A structural analysis of a unique family of tris Ni(0) stilbene complexes revealed a remarkable effect of the steric hindrance of the substituents at the para position of the stilbene unit to temperature, oxidation, and degradation in solution. From these analyses, Ni(4?tBustb)3 arose as a long-term air-, bench-. and temperature-stable Ni(0) complex. Importantly, Ni(4?tBustb)3 presents faster kinetic profiles and a broader scope as a Ni(0) source, thus outperforming the previously described Ni(4?CF3stb)3 in a variety of relevant Ni-catalyzed transformations.

Dual Gold-Catalyzed Formal Tetradehydro-Diels–Alder Reactions for the Synthesis of Carbazoles and Indolines

This work reports a dual gold-catalyzed tetradehydro-Diels–Alder reaction for the synthesis of nitrogen-containing aromatic heterocycles. Under the catalytic system (IPrAuNTf2/DIPEA), indolines and carbazoles as well as other N-containing aromatic heterocycles were prepared in high yields with good functional group tolerance. Unlike the traditional thermal tetradehydro-Diels–Alder reactions, diluted reaction concentration and radical prohibitors are not required for this protocol. Experimental data support a mechanism involving gold vinylidene species, which undergoes a 6 π electrocyclization, followed with 1,2-hydrogen shift.

Replacement of the hydrophobic part of 9-cis-retinoic acid with cyclic terpenoid moiety results in RXR-selective agonistic activity

Retinoid X receptor (RXR) agonists are interesting candidates for the treatment of metabolic syndrome. 9-Cis-retinoic acid (9cRA: 1) is a natural RXR agonist, that also works as a retinoic acid receptor (RAR) agonist. This fact prompted us to study the st

Caesium fluoride-promoted Stille coupling reaction: An efficient synthesis of 9Z-retinoic acid and its analogues using a practical building block

A highly efficient and rapid total synthesis of 9Z-retinoic acid was accomplished by caesium fluoride-promoted Stille coupling reaction; using a common building block, 9Z-retinoic acid analogues were also prepared by the same method without isomerisation of the Z-double bond. The Royal Society of Chemistry 2008.

Stereocontrolled synthesis of 6-s-cis- and 6-s-trans-locked 9Z-retinoids by hydroxyl-accelerated Stille coupling of (Z)-tri-n-butylstannylbut-2-en-1-ol and bicyclic dienyl triflates

Analogues of 9-cis-retinoic acid with locked 6-s-cis and 6-s-trans conformations have been stereoselectively synthesized using a Stille coupling reaction between bicyclic dienyl triflates (5 and 6, respectively) and (Z)-tributylstannylbut-2-en-1-ol (7) to stablish the Z geometry of the polyenic side chain. The mild conditions (25 °C, 30 min) of this coupling stand in contrast to the reluctance of the isomeric (E)-tributylstannylbut-2-en-1-ol (18) to react with triflates 5/6. The significant rate differences experimentally observed in Stille reactions between isomeric (Z)- and (E)-tri-n-butylstannylalkenols in favor of the former isomer, even with highly hindered alkenyl triflates, is ascribed to internal coordination of palladium to the heteroatom in the presumably rate-limiting transmetalation step. Dienals and trienals with an E geometry, which are not efficiently available by direct coupling of the corresponding triflates and E-stannanes, can in turn be obtained by isomerization of their Z-isomers.

Regiocontrolled Cyclohexenone Annulation via Acylation of a Ketone Carbonyl

1-(1-Ethoxyvinyl)cycloalkenes, readily available by palladium-catalyzed condensation of enol triflates with ethyl vinyl ether or its α-trimethylstannyl derivative, enter into Diels-ALder reaction with (Z)-1,2-bis(phenylsulfonyl)ethylene.These adducts unde