51534-73-7

Upstream product

• 51534-67-9 2-(2-Methanesulfinyl-2-methylsulfanyl-ethyl)-cyclohexanone 
• 704-99-4 2-(3-methylbut-2-en-1-yl)cyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 109-92-2 ethyl vinyl ether 
• 108-94-1 cyclohexanone 
• 10468-40-3 cyclohexanone N-cyclohexylimine 
• 1056477-06-5 2-bromocyclohexanone 
• 41302-34-5 2-(methoxycarbonyl)cyclohexanone 
• 58648-11-6 methyl 2-allyl-2-cyclohexanonecarboxylate 
• 10424-93-8 N'-cyclohexylidene-N,N-dimethyl-hydrazine 
• 94-66-6 2-allylcyclohexan-1-one 
• 74327-26-7 (Cyclohexanonyl-2')ethanaldiethylacetal 

Downstream Products

• 10198-27-3 2-(2-hydroxyethyl)-cyclohexan-1-one 
• 27345-72-8 trans-2-(2-hydroxyethyl)cyclohexanol 
• 24682-42-6 cis-2-(2-Hydroxyethyl)cyclohexanol 
• 13618-91-2 4,5,6,7-tetrahydroindole 
• 24682-42-6 2-(2'-hydroxyethyl)cyclohexan-1-ol 

Relevant academic research and scientific papers

Dibromo-BODIPY as an Organic Photocatalyst for Radical-Ionic Sequences

A new dibrominated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is reported as a new metal-free photocatalyst. This BODIPY showed similar optoelectronic, electrochemical, and performance properties to those of Ru(bpy)3Cl2, one of the most common photocatalysts in a known radical-ionic transformation, such as the formation of 1,4-dicarbonyl compounds. Moreover, additional sequences in which the generated oxonium ion is trapped by an internal nucleophile were developed using this BODIPY photocatalyst. These new sequences allowed the straightforward preparation of ?3-alkoxylactones, monoprotected 1,4-ketoaldehydes, and dihydrofurans. This new catalyst, the methodology, and the forged functional groups could be important tools in organic synthesis.

Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis

A transformation of fluxional into configurationally stable axially chiral N-arylpyrroles was achieved with a highly atroposelective electrophilic aromatic substitution catalyzed by a chiral-at-metal rhodium Lewis acid. Specifically, N-arylpyrroles were alkylated with N-acryloyl-1H-pyrazole electrophiles in up to 93 percent yield and with up to >99.5 percent ee, and follow-up conversions reveal the synthetic utility of this new method. DFT calculations elucidate the origins of the observed excellent atroposelectivity.

Visible-Light Photocatalytic Preparation of 1,4-Ketoaldehydes and 1,4-Diketones from α-Bromoketones and Alkyl Enol Ethers

A Ru2+-photocatalyzed, visible-light-mediated ATRA reaction for the straightforward preparation of 1,4-ketoaldehydes, 1,4-diketones, and 1,4-ketoesters, which are of difficult access by other means, is reported herein. This method employs readily accessible α-bromoketones and alkyl vinyl ethers as starting materials, allowing the construction of secondary, tertiary, and challenging quaternary centers. In addition, the synthetic usefulness of this method is illustrated by applying it to the construction of substituted pyrroles.

Synthesis of 5-substituted 4,5,6,7-tetrahydroindoles from cyclohexanones

5-Substituted 4,5,6,7-tetrahydroindoles were prepared from 4-substituted cyclohexanones in three steps: conversion to an enol silyl ether, introduction of a formylmethyl group at 2-C, and the Paal-Knorr pyrrole synthesis by reacting the 1,4-dicarbonyl compounds with ammonia. The substituents are H, methyl, ethyl, tert-butyl, methoxy, and phenyl.

Cyclization of unsaturated amides with triflic anhydride and samarium diiodide

A new approach to the generation of acyl radical equivalents has been developed. Treatment of amides with triflic anhydride followed by samarium diiodide allows for cyclization onto appropriately substituted olefins.

Synthesis of 3-hydroperoxy (or hydroxy)-substituted 1,2-dioxanes and 1,2-dioxepanes by the ozonolysis of unsaturated hydroperoxy acetals

Mono-ozonolysis of dienes in methanol gave in each case the corresponding unsaturated hydroperoxy acetals. The reaction of the hydroperoxides with ozone in the solvent system such as AcOH-CH2Cl2 resulted in the production of the corr

Neighboring Group Participation in Lewis Acid-Promoted and Annulations. The Stereocontrolled Synthesis of Tricyclic Ethers

A variety of 1,4- and 1,5-keto aldehydes derived from cycloalkanes are coupled with the bis(trimethylsilyl) enol ether of methyl acetoacetate in the presence of either TMSOTf or TrSbCl6 to generate tricyclic ethers.The reactions proceed with excellent regiochemical control by a mechanism involving neighboring group participation.This mechanism involves initial formation of a bicyclic oxocarbenium ion intermediate from the keto aldehyde substrates.The geometries of selected bicyclic intermediates have been optimized using the AM1 method allowing successful prediction of the stereochemical outcomes in the cyclization in most cases.Epimerization of α-chiral keto aldehyde substrates does not appear to occur in these Lewis acid-promoted annulation reactions.