83803-22-9

Upstream product

• 10458-14-7 (2R,5S)-menthone 
• 13154-14-8 1-propenylmagnesium bromide 
• 33651-09-1 (1S,2S,5R)-2-i-propyl-5-methyl-1-(1-propyn-1-yl)cyclohexan-1-ol 
• 83803-23-0 Propionic acid (1S,2S,5R)-2-isopropyl-5-methyl-1-((E)-propenyl)-cyclohexyl ester 
• 6386-72-7 (E)-propenyl lithium 
• 369651-27-4 (1S,2S,5R)-1-allyl-2-isopropyl-5-methylcyclohexanol 
• 401515-97-7 2-pyridylmethyl formate 
• 60573-68-4 3-pyridyllithium 
• 217321-04-5 Carbonic acid (1R,2S,5R)-2-isopropyl-5-methyl-1-((E)-propenyl)-cyclohexyl ester methyl ester 
• 590-15-8 trans-2-propenyl bromide 

Downstream Products

• 83803-23-0 Propionic acid (1S,2S,5R)-2-isopropyl-5-methyl-1-((E)-propenyl)-cyclohexyl ester 
• 217321-04-5 Carbonic acid (1R,2S,5R)-2-isopropyl-5-methyl-1-((E)-propenyl)-cyclohexyl ester methyl ester 
• 306973-57-9 (1S,4R)-1-Isopropyl-4-methyl-2-[(R)-2-methyl-hex-5-en-(E)-ylidene]-cyclohexane 
• 217321-16-9 (1S,4R)-2-[(R)-2-Cyclohexyl-prop-(E)-ylidene]-1-isopropyl-4-methyl-cyclohexane 
• 217321-15-8 {(S)-2-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidene]-1-methyl-ethyl}-benzene 
• 217321-12-5 (1S,4R)-1-Isopropyl-4-methyl-2-[(R)-2-methyl-hex-(E)-ylidene]-cyclohexane 
• 217321-14-7 (1S,4R)-1-Isopropyl-4-methyl-2-[(S)-2,3,3-trimethyl-but-(E)-ylidene]-cyclohexane 
• 217321-10-3 (1S,4R)-1-Isopropyl-4-methyl-2-[(R)-2-methyl-but-(E)-ylidene]-cyclohexane 
• 693833-41-9 (1S,4R)-2-[(2R,4S,6S)-7-tert-Butoxy-2,4,6-trimethyl-hept-(E)-ylidene]-1-isopropyl-4-methyl-cyclohexane 
• 693833-32-8 (1S,4R)-2-[(2R,4S)-5-tert-Butoxy-2,4-dimethyl-pent-(E)-ylidene]-1-isopropyl-4-methyl-cyclohexane 
• 693833-30-6 (1S,4R)-2-[(S)-3-tert-Butoxy-2-methyl-prop-(E)-ylidene]-1-isopropyl-4-methyl-cyclohexane 

Relevant academic research and scientific papers

Investigations of the scope and mechanism of the tandem hydroesterification/lactonization reaction

(Chemical Equation Presented) Heating allylic and homoallylic alcohols and 2-pyridylmethyl formate in the presence of Ru3(CO)12 initiates a tandem sequence of hydroesterification and lactonization. Mechanistic studies suggest that regioselectivity and overall reaction efficiency are governed by the relative rates of reductive elimination and β-hydride elimination for the alkylruthenium intermediates.

An iterative approach to three fragments of ionomycin

The SN2′ displacement of menthone-derived allylic carbonates with cuprate reagents occurs with high diastereoselectivity. This method can be used in an iterative fashion to construct stereocenters bearing a 1,3-relationship in a carbon chain. E

Chiral α-substituted carbonyls and alcohols from the S(N)2' displacement of cuprates on chiral carbonates: An alternative to the alkylation of chiral enolates

A highly stereoselective sequence of reactions, based on the anti-selective S(N)2' addition of cuprates to allylic carbonates, transforms alkynes or alkenyl halides into carbonyls having α-chiral centers. The method, which uses menthone as a chiral auxiliary, is a useful alternative to the alkylation of chiral enolates with the added advantage of allowing for the 'alkylation' of sec- and tert-alkyl and aryl groups.

A Nonresolutive Approach to the Preparation of Configurationally Pure Difunctional Molecules

Treatment of menthone (5) with organometallic reagents affords axial tertiary alcohols of type 6 with high diastereoselectivity.Propionate 12, derived from trans-11, undergoes an enolate Claisen rearrangement with complete transfer of chirality.The use of