122091-56-9Relevant academic research and scientific papers
A asymmetric catalytic synthesis of (R)- 4, 7 - dimethyl - 1 - Tetralone method
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, (2017/08/25)
The invention discloses a method for asymmetrically catalyzing and synthesizing (R)-4, 7-dimethyl-1-tetralone. According to the method, an asymmetrical Kumada cross coupling reaction is conducted on racemization 2-halogenated propionate ester catalyzed by bis oxazoline/ cobalt and a methyl phenyl grignard reagent, and (S)-P-toluene propionate ester 2 is firstly generated; then, (S)-P-toluene propionate ester 2 is reduced to (S)-P-toluene propyl alcohol 3 through diisobutylaluminium hydride (DIBAL-H), and then (R)-4-p-methylphenyl-1-amylene 5 is obtained through bromine generation and coupling with and vinyl grignard reagent; next, a hydroboration-oxidation reaction and a Dess-Martin oxidizing reaction are sequentially conducted, and (R)-4-p-methylphenyl valeraldehyde 6 is obtained; finally, oxidation is conducted through silver oxide, an intramolecular Fourier acyl reaction is conducted, and (R)-4,7-dimethyl-1-tetralone is obtained in a ring-closure synthesis mode. The synthesis route is simple and concise, 8 reactions are conducted in all, the total yield is 27%, and the optical purity of a product is 90%.
A asymmetric catalytic synthesis (S)- aryl curcumene method
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, (2017/08/25)
The invention discloses a method for asymmetrically catalyzing and synthesizing (S)-curcumene. According to the method, racemization 2-halogenated propionate ester serves as a starting material, under the catalysis of bis oxazoline/ cobalt, an asymmetrica
Asymmetric synthesis of (R)-ar-curcumene, (R)-4,7-dimethyl-l-tetralone, and their enantiomers via cobalt-catalyzed asymmetric Kumada cross-coupling
Wu, Lin,Zhong, Jiang-Chun,Liu, Shi-Kuo,Liu, Fei-Peng,Gao, Zi-Dong,Wang, Min,Bian, Qing-Hua
, p. 78 - 83 (2015/12/31)
An efficient and concise asymmetric synthesis of (R)-(+)-ar-curcumene, (R)-4,7-dimethyl-l-tetralone, and their enantiomers was accomplished. The key step to construct the stereogenic benzylmethyl centers of these natural products is the cobalt-catalyzed a
Iridium-catalyzed asymmetric hydrogenation of 3,3-disubstituted allylic alcohols in ethereal solvents
Bernasconi, Maurizio,Ramella, Vincenzo,Tosatti, Paolo,Pfaltz, Andreas
, p. 2440 - 2444 (2014/03/21)
Ir-phosphinomethyl-oxazoline complexes have been identified as efficient, highly enantioselective catalysts for the asymmetric hydrogenation of 3,3-disubstituted allylic alcohols and related homoallylic alcohols. In contrast to other N,P ligand complexes, which require weakly coordinating solvents, such as dichloromethane, these catalysts perform well in more ecofriendly THF or 2-MeTHF. Their synthetic potential was demonstrated with the formal total synthesis of four bisabolane sesquiterpenes. Particularly high enantioselectivity values in the asymmetric hydrogenation of 3,3-disubstituted allylic alcohols and related homoallylic alcohols have been achieved with Ir-phosphinomethyloxazoline catalysts. In contrast to other N,P-ligand complexes, which require weakly coordinating solvents, such as CH 2Cl2, these catalysts perform well in more ecofriendly THF or 2-MeTHF (see scheme; CODa =a 1,5-cyclooctadiene). Copyright
Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes
Aggarwal, Varinder K.,Ball, Liam T.,Carobene, Simon,Connelly, Rickki L.,Hesse, Matthew J.,Partridge, Benjamin M.,Roth, Philippe,Thomas, Stephen P.,Webster, Matthew P.
, p. 9230 - 9232 (2012/09/10)
The expedient enantioselective synthesis of 5 bisabolane sesquiterpenes has been achieved using a common, one-pot lithiation-borylation reaction of secondary benzylic carbamates and either protodeboronation or oxidation to give the natural products in few
Enantioselective synthesis of (+)-nuciferal, (+)-(E)-nuciferol and (+)-α-curcumene by chiral hydrogenesterification reaction
Du, Zhenfing,Yue, Guoren,Ma, Junying,She, Xuegong,Wu, Tongxing,Pan, Xinfu
, p. 427 - 429 (2007/10/03)
Using chiral hydrogenesterification reaction as the key step, the stereoselective synthesis of (+)-nuciferal 1, (+)-(E)-nuciferol 2 and (+)-a-curcumene 3 has been achieved.
Enantiodivergent Route to the Aromatic Bisabolane Sesquiterpenes by Regio- and Stereo-controlled Epoxide Opening
Takano, Seiichi,Yanase, Masashi,Sugihara, Takumichi,Ogasawara, Kunio
, p. 1538 - 1540 (2007/10/02)
An enantiodivergent route to aromatic bisabolane sesquiterpenes from a single chiral precursor has been established by employing regio- and stereo-controlled epoxide opening as the key step.
THE FIRST STEREOSELECTIVE SYNTHESIS OF (+)-NUCIFEROL AND (+)-NUCIFERAL
Takano, Seiichi,Goto, Emiko,Ogasawara, Kunio
, p. 5567 - 5570 (2007/10/02)
Using (S)-benzyl 2,3-epoxypropyl ether (1), the first stereoselective synthesis of (+)-nuciferol (14) and (+)-nuciferal (16) has been achieved.Employing the same methodology an enantioselective synthesis of (+)-α-curcumene (17) is also described.
