117894-23-2

Upstream product

• 117894-21-0 (3R,5R)-3-phenyl-5-trimethylsilylcyclohexanone 
• 217310-17-3 (S)-3-Isopropoxy-5-isopropyl-cyclohex-2-enone 
• 35376-41-1 5-phenylcyclohex-2-en-1-one 
• 557-20-0 diethylzinc 
• 14371-10-9 (E)-3-phenylpropenal 
• 1694-31-1 tert-butyl acetoacetate 
• 116215-94-2 (R)-(-)-5-trimethylsilyl-2-cyclohexenone 
• 542-05-2 acetonedicarboxylic acid 
• 104-55-2 3-phenyl-propenal 
• 18456-87-6 5-isopropyl-1,3-cyclohexanedione 
• 844885-47-8 (S)-2-cyano-5-oxo-3-phenylhexanoic acid methyl ester 
• 844885-65-0 (R)-5-oxo-3-phenylhexanenitrile 
• 56917-71-6 5-trimethylsilyl-2-cyclohexanone 
• 98-80-6 phenylboronic acid 

Downstream Products

• 26114-87-4 (1R,5R)-5-phenyl-2-cyclohexenol 
• 921199-71-5 (R)-5-oxo-3-phenylhexanal 
• 479543-87-8 (3R,5R)-3-methyl-5-phenylcyclohexan-1-one 

Relevant academic research and scientific papers

Enantiodivergent preparation of optically pure tricyclic cyclohexanoids via lipase-mediated asymmetrization of a meso-symmetric starting material

Two potentially useful, optically pure, tricyclohexanoids having 1,4-ethanohydronaphthalen-5-one system have been prepared in an enantiodivergent way from a single chiral tricyclic cyclohexanoid precursor obtained by lipase-mediated asymmetrization of a m

Synergistic Cu-amine catalysis for the enantioselective synthesis of chiral cyclohexenones

An unprecedented utilization of 1,3-acetonedicarboxylic acid as a 1,3-bis-pro-nucleophile and a reactive acetone surrogate in enantioselective catalysis has been reported. By synergistically activating the ketodiacid by copper catalysis and an α,β-unsatur

Enantioselective Synthesis of cis-Decalin Derivatives by the Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones

A novel strategy for the synthesis of cis-decalins by an ytterbium-catalyzed asymmetric inverse-electron-demand Diels–Alder reaction of 2-pyrones and silyl cyclohexadienol ethers is reported here. A broad range of synthetically important cis-decalin derivatives with multiple contiguous stereogenic centers and functionalities are obtained in good yields and stereoselectivities. A full set of diastereomeric substituted cis-decalin motifs are readily accessible by tuning the absolute configurations of substituted silyl cyclohexadienol ethers (R or S) as well as the ligands (R or S). The synthetic potential is showcased by the enantioselective total synthesis of 4-amorphen-11-ol, and further demonstrated by the first total synthesis of cis-crotonin.

Kinetic resolution of 5-substituted cycloalkenones by peptidic amidophosphane-copper-catalyzed asymmetric conjugate addition of dialkylzinc

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

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

Asymmetric synthesis of 5-arylcyclohexenones by rhodium(I)-catalyzed conjugate arylation of racemic 5-(trimethylsilyl)cyclohexenone with arylboronic acids

(Chemical Equation Presented) A catalytic asymmetric conjugate arylation of racemic 5-(trimethylsilyl)cyclohex-2-enone with arylboronic acids was catalyzed by 3 mol % chiral amidophosphane- or BINAP-Rh(I) in dioxane-water (10:1) to afford trans- and cis-3-aryl-5-(trimethylsilyl)cyclohexanones in high enantioselectivity. Dehydrosilylation of the product mixture with cupric chloride in DMF gave 5-arylcyclohex-2-enones with up to 93% ee in good yield. Enantiofacial selectivity with chiral phosphane-Rh(I) exceeds the trans-diastereoselectivity that is maintained in the achiral or racemic phosphane-Rh(I)-catalyzed conjugate arylation of 5-(trimethylsilyl) cyclohexenone.

Highly enantioselective conjugate additions to α,β-unsaturated ketones catalyzed by a (salen)Al complex

Chiral (salen)Al complex 1a catalyzes the highly enantioselective conjugate addition of carbon-and nitrogen-based nucleophiles to acyclic α,β-unsaturated ketones. This methodology is tolerant of substantial variation of the ketone structure, providing acc

Highly enantioselective copper-phosphoramidite catalyzed kinetic resolution of chiral 2-cyclohexenons

A variety of substituted 2-cyclohexenones, such as (R)-1, is obtained enantiomerically pure by employing the chiral copper-phoshoramidite complex [Cu(OTf)2L*] as a highly efficient catalyst for their kinetic resolution (>99% ee at 52% conversion, selectively S>200). These important building blocks can be obtained on a synthetically interesting scale, as was demonstrated by the successful multigram resolution of 5-methyl-2-cyclohexenone. Tf = trifluoromethanesulfonyl.

Photochemical rearrangement of 2-phenylthio-3-aminocyclohexanols. New access to deoxyazasugars and their derivatives

This paper reports the regioselective photorearrangement of 2- phenylthio-3-aminocyclohexanols to deoxyazasugars and their derivatives. These give access to variously substituted piperidines, amino-sulfones, - sulfoxides and -acids.

SYNTHESIS OF (+)-α-CURCUMENE, (+)-CURCUMONE AND (-)-METHYL CITRONELLATE STARTING FROM OPTICALLY PURE 5-TRIMETHYLSILYL-2-CYCLOHEXENONE

1,4-addition of Grignard reagents in the presence of chlorotrimethylsilane to 5-trimethylsilyl-2-cyclohexanone (1) proceeded in a highly diastereoselective manner to give trans adducts in high yields. (+)-α-Curcumene, (+)-curcumone and (-)-methyl citronellate were synthesized starting from optically pure 1.