58070-37-4

Upstream product

• 42798-04-9 2-isopropenylcyclohexanone ethylene ketal 
• 94417-55-7 2-(1-Methyl-1-methylselanyl-ethyl)-cyclohexanone 
• 80533-41-1 2-<1-hydroxy-1-methyl-2-(phenylseleno)ethyl>cyclohexanone 
• 13291-18-4 isopropenylmagnesium bromide 
• 822-87-7 2-Chlorocyclohexanone 
• 108-94-1 cyclohexanone 
• 286-20-4 cyclohexane-1,2-epoxide 
• 57524-90-0 3-methylcyclohexanone lithium enolate 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 286-20-4 cyclohexene oxide 
• 24350-58-1 (±)-(1S,2R)-2-(prop-1-en-2-yl)cyclohexanol 

Downstream Products

• 13747-75-6 2-isopropenyl-2-methyl-cyclohexanone 
• 1415637-00-1 (E)-1-methoxy-8-methyl-10-phenyl-3,4,5,6,9,10-hexahydroazecin-2(1H)-one 
• 1415637-02-3 (E)-12-methyl-3,4,7,8,9,10,13,13a-octahydro-1H-pyrido[1,2-a]azecin-6(2H)-one 
• 78782-41-9 C₅H₅Fe(CO)2CH₂C(CH₃)C₆H₈(CH₃)O⁽¹⁺⁾*BF₄^(1-) 
• 1392283-81-6 (E)-8-methyl-10-(4-nitrophenyl)-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one 

Relevant academic research and scientific papers

Total Synthesis of Laingolide A Diastereomers

The first total syntheses of two (±)-laingolide A diastereomers were achieved in 11 and 12 steps, respectively. The key steps include a tandem cross-dimerization/oxonia-Cope reaction and an intramolecular dehydrative cyclization for the formation of either the trans- or cis-enamide moieties.

Enantioselective catalytic transannular ketone-ene reactions

Highly enantio-and diastereoselective transannular ketone-ene reactions are catalyzed by a new chromium(III) triflate tridentate Schiff base complex. Electronically unactivated keto-olefins undergo heteroene reactions at ambient temperature to afford enantioenriched bicyclic alcohols, common structural motifs in natural products. The kinetic resolution of a configurationally stable planar-chiral cyclodecenone is also described.

Stereocontrolled synthesis of carbocycles via four successive pericyclic reactions

Herein, we report a highly diastereoselective construction of fused carbocycles using four successive pericyclic reactions. The Royal Society of Chemistry.

Pd(OAc)2/P(cC6H11) 3-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation

Allylations of aryl halides take place upon treatment of tertiary homoallyl alcohols with aryl halides in the presence of cesium carbonate and a palladium catalyst. The allylation reaction would consist of the following steps: (1) oxidative addition of ar

Synthesis of the C7-C15 trans decalin portion of the natural antibiotic tetrodecamycin

(Chemical Equation Presented) The tandem oxy-Cope/ene/Claisen rearrangement has been developed in our laboratory as a powerful method for rapid construction of complex Decalin cores. Herein, we describe the use of this method to generate the Decalin core

Tandem oxy-Cope/transannular ene reaction of 1,2-divinylcyclohexanols

Graph Presented The syntheses via tandem oxy-Cope/transannular ene reaction of 1,2-divinylcyclohexanols to bi-and tricyclic skeletons are described. This strategy generates a rapid method for the preparation of advanced polycyclic intermediates with high

Vinylation of cyclohexanone enolates using vinyl ether-iron complexes. Diastereoselectivity of carbon-carbon bond formation

Cationic vinyl ether-iron complexes 1, isolated as stable BF4- salts, are readily available from α-halo acetals and ketals. The olefin ligand in these complexes is unsymmetrically bound to the metal, which accounts for the relatively low barrier for rotation about the formal double bond, which is observed in these substances (15-23 kcal/mol), and for the high regioselectivity with which nucleophiles add to the activated olefinic center. The salts 1 serve as vinylating, isopropenylating, and cis-propenylating reagents with cyclohexanone enolates. Reaction of 1a with cyclohexanone enolate gave a single diastereomeric product 5. This has been converted to the lactone 10, which establishes the relative configuration of the adjacent chiral centers in 5. The relative configuration of analogous chiral centers in the major diastereomer 16a, formed by the alkylation of 3-methylcyclohexanone enolate with 1a, has been established by a single-crystal X-ray diffraction study and shown to be identical with that in 5. Complex 1a also gives a single diastereoisomeric adduct with 6-methylcyclohexanone enolate, and this has been shown by 13C NMR studies to have the same relative configuration at the newly formed chiral centers as in 5 and 16a. Alkylation of 5-methylcyclohexanone enolate with 1b leads to a mixture of isopulegone and isoisopulegone, while alkylation of the kinetic enolate derived from 3-methyl-2-cyclohexenone with this complex yields isopiperitenone.

SELENIUM STABILIZED CARBENIUM IONS. LEWIS ACID MEDIATED SELENO-ALKYLATION OF KETONES

Silyl enol ethers of ketones can be successfully selenoalkylated by Lewis acid activated seleno-ketals; the product β-seleno-ketones undergo interesting oxidation-deselenation reactions.

α Vinylation of Ketones. A General Method Using a (Phenylseleno)acetaldehyde

(Phenylseleno)acetaldehyde can be used as a synthetic equivalent of the vinyl carbonium ion, CH2=CH2+.A number of ketone enolates, usually as zinc salts, were condensed with (phenylseleno)acetaldehyde to give β-hydroxy selenides (average yield

New Method for Preparing βγ-Unsaturated Ketones: Use of Phenylselenoacetaldehyde

Zinc enolates derived from ketones condense efficiently with phenylselenoacetaldehyde and the products are converted into βγ-unsaturated ketones by the action of methanesulphonyl chloride and triethylamine.