217321-02-3

Upstream product

• 10458-14-7 (2R,5S)-menthone 
• 4843-72-5 (E)-2-phenylethenyllithium 
• 30094-01-0 β-styrylmagnesium bromide 
• 536-74-3 phenylacetylene 
• 100-52-7 benzaldehyde 
• 7436-90-0 2,2-dibromostyrene 
• 4440-01-1 lithium phenylacetylide 

Downstream Products

• 217321-09-0 Carbonic acid (1R,2S,5R)-2-isopropyl-5-methyl-1-((E)-styryl)-cyclohexyl ester methyl ester 
• 217321-19-2 {(R)-1-[(2S,5R)-2-Isopropyl-5-methyl-cyclohex-(E)-ylidenemethyl]-2,2-dimethyl-propyl}-benzene 
• 33124-21-9 (R)-3,3-Dimethyl-2-phenyl-1-butanol 

Relevant academic research and scientific papers

Chiral aminoalcohols with a menthane skeleton as catalysts for the enantioselective addition of diethylzinc to benzaldehyde

Novel chiral aminoalcohols were synthesized by highly diastereoselective addition of Me3SiCN and LiCH2CN to (-)-menthone followed by LiAlH4 reduction. The addition of CH2=CH-MgBr and PhCH=CH-MgBr to menthone and the following epoxidation, provided useful hydroxy epoxides, one of which could be aminolyzed to afford an aminodiol. In one case, the configuration of the newly formed epoxidic stereogenic center was determined by X-ray crystallography. When applied as catalysts in the enantioselective addition of Et2Zn to benzaldehyde, the aminoalcohols induced enantiomeric excesses (e.e.s) of up to 77%.

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.

Efficient syntheses of optically active 2-arylalkanoic acids

A highly enantioselective synthesis of 2-axylpropanoic acid was achieved, using a new developed methodology of cuprate addition to chiral carbonates derived from menthone.