236737-79-4Relevant academic research and scientific papers
Synthesis of functionalized 4a-methyl-1,2,3,4,4a,9,10,10a- octahydrophenanthrenes
Dyker, Gerald,Grundt, Peter
, p. 588 - 596 (1999)
The title compounds were constructed by a Heck reaction of functionalized aryl halides with homoallylic alcohols followed by Michael addition and subsequent cyclocondensation.
Organocopper-Triggered Cyclisation of Conjugated Diene-ynes: Diastereo- and Enantioselective Synthesis of Indenes
Arif, Tanzeel,Borie, Cyril,Tintaru, Aura,Naubron, Jean-Valre,Vanthuyne, Nicolas,Bertrand, Michle P.,Nechab, Malek
supporting information, p. 3611 - 3616 (2016/01/25)
Organocopper reagents react with readily available chiral conjugated diene-ynes to give indene derivatives bearing two stereogenic centres. The investigation of this original reaction in optically pure series demonstrates that a double transfer of chirality is operating. A stereocontrolled cascade involving SN2′ followed by carbocupration and conjugate addition reactions accounts for the total recovery of the initial chirality. The scope and limitations of the reaction were investigated. The high diastereofacial discrimination in the cyclisation step allowed the construction of the quaternary stereocentre with excellent dr and ee, with the opposite configuration depending on the E- or Z-configuration of the alkene in the starting material. Post-functionalisation of indenes allowed the synthesis of indanyl derivatives containing four contiguous stereocentres.
