64129-96-0

Upstream product

• 315208-16-3 (6S,9S)-γ-ionol 
• 52646-93-2 [(S)-2,6,6-trimethylcyclohex-2-enyl]methanol 
• 166022-30-6 (S)-(+)-2',2'-dimethyl-6'-methylene-1'-cyclohexylcarboxaldehyde 
• 113084-12-1 (1R,2R)-2-hydroxy-2,6,6-trimethyl-1-cyclohexanemethanol 
• 113084-08-5 (-)-2-hydroxy-2,6,6-trimethyl-1-cyclohexanecarbaldehyde 
• 73925-69-6 (-)-(1'S)-2',3'-dihydro-2'-hydroxy-α-ionone 
• 475197-97-8 (1'R,3'S)-cis-(3'-(imidazoylthiocarbonyl)oxy-2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methyl 2,2-dimethylpropyonate 
• 475197-95-6 (1'R,3'S)-(-)-cis-(3'-hydroxy-2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methyl 2,2-dimethylpropionate 
• 166022-29-3 (S)-(+)-(2',2'-dimethyl-6'-methylene-1'-cyclohexyl)methanol 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 49816-69-5 gamma-ionone 

Downstream Products

• 24190-33-8 (+)-(S)-dihydro-γ-ionone 
• 52612-51-8 (+)-(1'R,6'S)-4-(2',2',6'-trimethylcyclohexyl)butan-2-one 

Relevant academic research and scientific papers

Competitive Gold-Promoted Meyer-Schuster and oxy-Cope Rearrangements of 3-Acyloxy-1,5-enynes: Selective Catalysis for the Synthesis of (+)-(S)-γ-Ionone and (-)-(2S,6 R)-cis-γ-Irone

We report a simple, highly stereoselective synthesis of (+)-(S)-γ-ionone and (-)-(2S,6R)-cis-γ-irone, two characteristic and precious odorants; the latter compound is a constituent of the essential oil obtained from iris rhizomes. Of general interest in this approach are the photoisomerization of an endo trisubstituted cyclohexene double bond to an exo vinyl group and the installation of the enone side chain through a [(NHC)AuI]-catalyzed Meyer-Schuster-like rearrangement. This required a careful investigation of the mechanism of the gold-catalyzed reaction and a judicious selection of reaction conditions. In fact, it was found that the Meyer-Schuster reaction may compete with the oxy-Cope rearrangement. Gold-based catalytic systems can promote either reaction selectively. In the present system, the mononuclear gold complex [Au(IPr)Cl], in combination with the silver salt AgSbF6 in 100:1 butan-2-one/H2O, proved to efficiently promote the Meyer-Schuster rearrangement of propargylic benzoates, whereas the digold catalyst [{Au(IPr)}2(μ-OH)][BF4] in anhydrous dichloromethane selectively promoted the oxy-Cope rearrangement of propargylic alcohols.

Enantioselective synthesis of both enantiomers of γ-ionone, γ-damascone, karahana lactone and karahana ether

A straightforward enantioselective synthesis of both enantiomers of the title compounds is described starting from enantiopure methyl (2S,6R)- or (2R,6S)-cis-2-hydroxy-γ-cyclogeraniate. These versatile building blocks are obtained by biomimetic cyclizatio

Synthesis and olfactory evaluation of (+)- and (-)-γ-ionone

The synthesis of enantiomerically pure (+)- and (-)-γ-ionone 3 is reported. The first step in the synthesis is the diastereoisomeric enrichment of 4-nitrobenzoate derivatives of racemic γ-ionol 12. The enantioselective lipase-mediated kinetic acetylation

Synthesis and Absolute Stereochemistry of Chiral γ-Ionone and Dihydro-γ-ionone

The optical resolution of (+/-)-α-cyclogeranic acid (4) with (-)-α-methylbenzylamine gave (-)-(S)-α-cyclogeranic acid (4).Epoxidation of (-)-(S)-methyl α-cyclogeranate (5), followed by reduction with lithium aluminium hydride, gave mainly (-)-(1R,2R)-2-hydroxy-2,6,6-trimethyl-1-cyclohexanemethanol (7b), which was oxidized with pyridinium chlorochromate to give (-)-hydroxyaldehyde 8.The reaction of aldehyde 8 with 2-oxopropylidenetriphenylphosphorane gave (-)-(1'S,2'R)-2',3'-dihydro-2'-hydroxy-α-ionone (9).The thermal decomposition of (1'S)-2'-acetoxy-2',3'-dihydro-α-ionone (10) gave (-)-(S)-α-ionone (2) and (+)-(S)-γ-ionone (1).The partial hydrogenation of (+)-(S)-γ-ionone (1) gave (+)-(S)-dihydro-γ-ionone (3).