81417-98-3

Upstream product

• 764-59-0 hex-5-en-1-al 
• 931-50-0 cyclohexylmagnesium bromide 
• 1119-51-3 bromopentene 
• 2043-61-0 cyclohexanecarbaldehyde 
• 34164-50-6 4-penten-1-ylmagnesium bromide 

Downstream Products

• 1010081-71-6 (E)-7-cyclohexyl-7-hydroxyhept-2-enal 
• 39257-00-6 1-cyclohexylhex-5-en-1-one 
• 200641-10-7 (E)-1-Cyclohexyl-6-(toluene-4-sulfonyl)-hex-5-en-1-ol 
• 727665-63-6 2-(3-cyclohexyl-3-methoxycarbonylaminopropyl)acrylic acid methyl ester 
• 727665-57-8 (1-azidohex-5-enyl)cyclohexane 
• 727665-04-5 1-cyclohexylhex-5-enyl acetate 

Relevant academic research and scientific papers

A Re2O7catalyzed cycloetherification of monoallylic diols

A Re2O7catalyzed cycloetherification of monoallylic diols is described. The reaction features short reaction time, mild reaction conditions and exclusive E selectivity. A wide range of monoallylic alcohols with alkyl or aryl substituents on olefin smoothly undergo ring closure to deliver corresponding oxa-heterocycles. The reaction is also operationally simple and not sensitive to air and moisture.

Copper-catalyzed oxaziridine-mediated oxidation of C-H bonds

The highly regio- and chemoselective oxidation of activated C-H bonds has been observed via copper-catalyzed reactions of oxaziridines. The oxidation proceeded with a variety of substrates, primarily comprising allylic and benzylic examples, as well as one example of an otherwise unactivated tertiary C-H bond. The mechanism of the reaction is proposed to involve single-electron transfer to the oxaziridines to generate a copper-bound radical anion, followed by hydrogen atom abstraction and collapse to products, with regeneration of the catalyst by a final single-electron transfer event. The involvement of allylic radical intermediates was supported by a radical-trapping experiment with TEMPO.

Au-catalyzed cyclization of monoallylic diols

The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as -78° C with catalyst loadings as low as 0.1 mol % to provide the products in 79-99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.

Dibromomethane as one-carbon source in organic synthesis: A versatile methodology to prepare the cyclic and acyclic α-methylene or α-keto acid derivatives from the corresponding terminal alkenes

Ozonolysis of mono-substituted alkenes A-1 followed by reacting with a preheated mixture of CH2Br2-Et2NH affords α-substituted acroleins A-2 in good yields. Under very mild reaction conditions, these α-substituted acroleins A-2 can be easily converted to α-methylene esters A-4, which could be further converted to the corresponding α-keto esters A-5. This methodology can be also applied to the preparation of α-methylene lactones B-4, α-methylene lactams, and α-keto lactones B-5 with various ring sizes.

Diastereoselective synthesis of α,α'-disubstituted oxygen heterocycles

Treatment of the para -toluenesulfonyl iodide adducts of a series of I-substituted 5-hexenols with K[N(TMS)2]] gave 2,6-disubstituted tetrahydropyrans with excellent cis-diastereoselectivity. The corresponding pentenols gave the 2,5-disubstituted tetrahydrofurans as 1:1 cis:trans mixtures.

A Stereoselective Approach to 2,6-Disubstituted Tetrahydropyrans by Conjugate Addition Reactions of Vinyl Sulfones

A highly stereoselective synthesis of cis-2,6-disubstituted tetrahydropyrans from functionalised 5-hexen-1-ols has been developed. Free radical addition of para-toluenesulfonyl iodide to the hexenol and DBU-mediated elimination of HI from the intermediate β-iodosulfones gives vinyl sulfones: subsequent conjugate addition of the potassium alkoxide leads to a highly stereoselective (≥30:1) cyclisation.