66334-22-3

Upstream product

• 29517-58-6 1-allylcyclohexanecarbaldehyde 
• 19096-89-0 methoxymethylenecyclohexane 
• 110516-15-9 1-Methoxy-3-methyl-2-oxa-spiro[4.5]dec-3-ene-4-carboxylic acid ethyl ester 
• 110516-16-0 2-(1-[1,3]Dithian-2-yl-cyclohexyl)-3-oxo-butyric acid ethyl ester 
• 138469-42-8 Cyclohexylcarboxaldehyde cyclohexylimine 
• 932-89-8 2-cyclohexylidene ethanol 
• 1552-92-7 ethyl cyclohexylideneacetate 
• 110516-21-7 1-(1-[1,3]Dithian-2-yl-cyclohexyl)-propan-2-one 
• 66334-20-1 1-Acetyl-2-methoxyspiro<2.5>octan 
• 175662-26-7 1-(1-Vinyl-cyclohexyl)-propan-2-one 

Relevant academic research and scientific papers

Claisen rearrangement based methodology for the spiroannulation of a cyclopentane ring. Formal total synthesis of (±)-acorone and isoacorones

A Claisen rearrangement based methodology for spiroannulation of a cyclopentane ring to cyclic precursors and its application in the formal total synthesis of acorones 1 is described. Thus, Claisen rearrangement of 2-cycloalkylideneethanols 12 with 2-methoxypropene and a catalytic amount of mercuric acetate generates 4,4-substituted hex-5-en-2-ones 13. Ozonolytic cleavage of the terminal olefin in the enones 13 and intramolecular aldol condensation of the resulting keto-aldehydes 14 furnishes the spiroannulated compounds 15. (C) 2000 Elsevier Science Ltd.

Convenient Wacker oxidations with substoichiometric cupric acetate

A modification of the Wacker oxidation of terminal olefins to methyl ketones using substoichiometric amounts of Cu(OAc)2 as a redox shuttle reagent is described. The modified procedure is generally high yielding despite reduced levels of copper salt and convenient. Importantly, in a problematic case, the conditions suppressed acidic hydrolysis during oxidation of substrate (+)-5 containing an acetonide.

A simple strategy for spirocyclopentannulation of cyclic ketones. Formal total synthesis of (±)-acorone

A general and simple methodology for spirocyclopentannulation of cyclic ketones (or 4,4-disubstituted cyclopentenones from acyclic ketones) and its application in the synthesis of the spirodienone 7 via a prochiral precursor constituting a formal total synthesis of (±)-acorone (6), are described.

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.

Mn(III)-PROMOTED ANNULATION OF ENOL ETHERS AND ESTERS TO FUSED OR SPIRO 2-CYCLOPENTENONES

Manganese(III)-promoted addition of various 1,3-dicarbonyl compounds to enol ethers or terminal enol esters, followed by hydrolysis of the resulting adducts and base catalyzed aldol cyclization provides an effective process for the synthesis of a wide ran