54307-74-3Relevant academic research and scientific papers
A Concise Enantioselective Approach to Quassinoids
Thomas, William P.,Pronin, Sergey V.
supporting information, p. 118 - 122 (2022/01/08)
A synthetic approach to quassinoids is described. The route to the tetracyclic core relies on an efficient and selective annulation between two unsaturated carbonyl components that is initiated by catalytic hydrogen atom transfer from an iron hydride to an alkene. Application of this strategy allows for enantioselective synthesis of quassin, which is prepared in 14 steps from commercially available starting material.
A concise asymmetric total synthesis of (+)-fawcettimine
Zeng, Xin,Jia, Zhuqing,Qiu, Fayang G.
, (2020/09/16)
A straightforward and stereocontrolled total synthesis of (+)-fawcettimine was accomplished from the known (R)-5-methyl-2-cyclohexen-one in 11 steps. The synthesis features a palladium mediated cycloalkenylation of a silyl enol ether for assembling the 6/
Efforts toward the synthesis of (+)-Lyconadin A
Karella, Satish,Raghavan, Sadagopan
, (2020/08/10)
Abstract: Synthetic efforts toward the synthesis of (+)-lyconadin A are described. B-Alkyl Suzuki coupling is utilized for combining 2-iodo cyclohexenone with the piperidine subunit. The piperidine subunit is derived from 5-bromo-3-nicotinic acid, and iod
Total synthesis of TMS-ent-bisabolangelone
Riss, Bernard,Garreau, Marion,Fricero, Prisca,Podsiadly, Patricia,Berton, Nicolas,Buchter, Sophie
, p. 3202 - 3212 (2017/05/12)
The absolute configuration of bisabolangelone has been established by an eleven step total synthesis of the corresponding TMS protected antipode starting from (R)-(+)-pulegone. Comparison of the TMS-derivatives by GC on a chiral column, allowed us to assign the absolute configuration of the synthetic compound and thus of the corresponding natural product. The latter has been confirmed by the Mosher's ester analysis of the known secondary carbinol derivative.
Regioselective Iridium-Catalyzed Asymmetric Monohydrogenation of 1,4-Dienes
Liu, Jianguo,Krajangsri, Suppachai,Singh, Thishana,De Seriis, Giulia,Chumnanvej, Napasawan,Wu, Haibo,Andersson, Pher G.
, p. 14470 - 14475 (2017/10/24)
A highly efficient regio- and enantioselective monohydrogenation of 1,4-dienes has been realized using an iridium catalyst with a chiral N,P-ligand under mild conditions. The substrate scope was studied and included both unfunctionalized as well as functionalized substituents on the meta- or para-position. Substrates having substituents with functionalities such as silyl protected alcohols or ketals were monohydrogenated in high regioselectivity and high enantiomeric excess (up to 98% ee).
Kinetic resolution of chiral cyclohex-2-enones by rhodium(I)/binap- catalyzed 1,2- and 1,4-additions
Kolb, Andreas,Hirner, Sebastian,Harms, Klaus,Zezschwitz, Paultheo Von
supporting information; experimental part, p. 1978 - 1981 (2012/06/18)
The feasibility of kinetic resolutions of racemic monosubstituted cyclohex-2-enones by Rh/binap-catalyzed reactions was investigated. 1,2-Addition of AlMe3 to the 5-substituted derivatives furnished allylic alcohols in the matched case, while t
Asymmetric catalysis: Resin-bound hydroxyprolylthreonine derivatives in enamine-mediated reactions
Carpenter, Richard D.,Fettinger, James C.,Lam, Kit S.,Kurth, Mark J.
supporting information; experimental part, p. 6407 - 6410 (2009/03/11)
Control of stereochemistry is achieved using two TentaGel-bound di-tert-butoxyprotected hydroxyprolyl-threonine catalysts (see picture, sphere represents TentaGel). These catalysts mediate asymmetric tandem enamine/Michael reactions with high enantioselectivity and complete diastereoselectivity; the choice of catalyst depends on the desired absolute configuration. (Chemical Equation Presented).
Kinetic resolution of 5-substituted cycloalkenones by peptidic amidophosphane-copper-catalyzed asymmetric conjugate addition of dialkylzinc
Soeta, Takahiro,Selim, Khalid,Kuriyama, Masami,Tomioka, Kiyoshi
, p. 6573 - 6576 (2008/02/05)
Asymmetric conjugate alkylation reaction of racemic 5-substituted cyclohexenones with dialkylzinc reagents was catalyzed by 2-5 mol % of dipeptidic amidophosphane-Cu(MeCN)4BF4 in toluene at 0 °C for 20 min to recover enantioenriched
A simple asymmetric organocatalytic approach to optically active cyclohexenones
Carlone, Armando,Marigo, Mauro,North, Chris,Landa, Aitor,Jorgensen, Karl Anker
, p. 4928 - 4930 (2007/10/03)
Optically active 2,5-disubstituted-cyclohexen-2-one derivatives have been prepared in a one-pot process consisting of five reaction steps: an organocatalytic asymmetric conjugated addition of β-ketoesters to α,β-unsaturated aldehydes that proceeds in aque
Stereocontrol of 1,5-related stereocentres using an intermediate silyl group-the diastereoselectivity of nucleophilic attack on a double bond adjacent to a stereogenic carrying a silyl group
Fleming, Ian,Maiti, Pranab,Ramarao, Chandrashekar
, p. 3989 - 4004 (2007/10/03)
R-5-Methylcyclohex-2-enone 1 reacts successively with the phenyldimethylsilylzincate reagent and acetaldehyde to give with regiocontrol the aldols 7, dehydration of which creates the E-exocyclic double bond of the α-β-unsaturated ketone 2. Conjugate addition of the ethylcuprate reagent to this compound takes place with high (96 : 4) selectivity in favour of the R stereoisomer 12, hydrolysis of which gives (2R,3R,5S,2′ R)-2-(but-2′-yl)-3-dimethyl(phenyl)silyl-5-methylcyclohexanone 3. The oxime acetate of this ketone undergoes fragmentation in the presence of trimethylsilyl trifluoromethanesulfonate to give 3R,7R,5E-3,7-dimethylnon-5-enonitrile 4, in which an open-chain 1,5-stereo-chemical relationship is set up with a high level of stereocontrol. A similar sequence adding 4-methylpentylcuprate to the enone 2, and fragmentation gives 3R,7R,5E-3,7,11-trimethyldodec-5-enonitrile 20. Reduction and hydrogenation of this nitrile gives 3R,7R-3,7,11 -trimethyldodecanal 22, which can be converted into phytol 25. The ketoaldehyde 29 reacts with samarium iodide to give only the alcohol 30, in which the radical anion has attacked from the top surface, just like the cuprate reagents in their reactions with the ketone 2.
