221046-97-5

Upstream product

• 815581-84-1 tert-Butyl-[(E)-(S)-1-methyl-3-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-allyloxy]-diphenyl-silane 
• 86561-84-4 essigsaeure-<(E,R)-6,7-dihydroxy-3,7-dimethyl-2-octenyl>ester 
• 86561-83-3 (S,E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol 
• 14398-36-8 (3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one 
• 127-41-3 alpha-ionone 
• 25312-34-9 alpha-ionol 
• 815581-77-2 [(1S,5R)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl]methyl 4-bromobenzoate 
• 815581-82-9 1-[((S)-2,6,6-trimethylcyclohex-2-enyl)methylsulfonyl]benzene 
• 815581-75-0 (1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol 
• 52646-93-2 [(S)-2,6,6-trimethylcyclohex-2-enyl]methanol 
• 69297-41-2 ((S)-2,6,6-Trimethyl-cyclohex-2-enylmethylsulfanyl)-benzene 
• 815581-83-0 (S)-1-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxy)-1-((S)-2,6,6-trimethyl-cyclohex-2-enyl)-butan-2-ol 
• 1026627-42-8 4-Bromo-benzoic acid (1R,5S)-5-methanesulfonyloxy-2,6,6-trimethyl-cyclohex-2-enylmethyl ester 
• 815581-78-3 [(R)-2,6,6-trimethylcyclohexa-2,4-dienyl]methyl 4-bromobenzoate 

Downstream Products

• 14398-36-8 (3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one 

Relevant academic research and scientific papers

Method for producing optically active α-ionone

Provided that a method for inexpensively producing optically active α-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active α-ionone obtained by the aforementioned method. A method for producing optically active α-ionone, comprising allowing α-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained α-ionone enol ester; a method for producing optically active α-ionone comprising subjecting α-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active α-ionol to react with an esterification agent to give an optically active α-ionol ester, hydrolyzing the obtained optically active α-ionol ester after purification as necessary, and then oxidizing the obtained optically active α-ionol; and a perfume composition comprising thus obtained optically active α-ionone.

A simple and efficient highly enantioselective synthesis of α-ionone and α-damascone

An efficient highly enantioselective (ee ≥99%) synthesis of α-ionone and α-damascone is described. Both enantiomers of title compounds were synthesized through two straightforward pathways diverging from enantiopure (R)- or (S)-α-cyclogeraniol. These versatile building blocks were obtained by regioselective ZrCl4-promoted biomimetic cyclization of (6S)- or (6E)-(Z)-6,7-epoxygeraniol, respectively, followed by deoxygenation of the so formed secondary alcohol. The chiral information was encoded by a highly regioselecive Sharpless asymmetric dihydroxylation of inexpensive geranyl acetate.

Enzyme-mediated synthesis of (R)- and (S)-α-ionone

Diastereoisomeric enrichment through fractional crystallisation of 4-nitrobenzoate derivatives of α-ionol, and enantioselective enzyme-mediated reactions of α-ionol and α-ionol acetate, were usefully combined to optimise two different procedures to enantiopure (S)- and (R)-ionone.