153060-96-9

Upstream product

• 815581-75-0 (1S,5R)-5-(hydroxymethyl)-4,6,6-trimethylcyclohex-3-enol 
• 140479-10-3 (+)-(5S)-2,5,6,6-tetramethylcyclohex-2-en-1-one 
• 163890-83-3 (-)-(R)-2,5,6,6-tetramethylcyclohexa-2,6-diene-1-methanol 
• 140632-38-8 (+)-(3R,7S)-4,7,8,8-tetramethyl-1-oxaspiro<2.5>oct-4-ene 

Downstream Products

• 89888-03-9 (E,2S,6R)-(-)-cis-α-irone 
• 108032-56-0 (Z,2S,6R)-(-)-cis-α-irone 
• 140632-41-3 (+)-(1R,3S)-2,2,3-trimethyl-6-methylidenecyclohexane-1-carbaldehyde 
• 153060-93-6 (-)-(1R,3S)-2,2,3-trimethyl-6-methylidenecyclohexane-1-methanol 
• 152944-60-0 (-)-(5S)-2,5,6,6-tetramethylcyclohex-1-ene-1-carbonyl chloride 
• 152944-59-7 (-)-(5S)-2,5,6,6-tetramethylcyclohex-1-ene-1-carboxylic acid 
• 153061-00-8 (-)-(5S)-2,5,6,6-tetramethylcyclohex-1-ene-1-carbaldehyde 
• 90242-81-2 (+)-(2S:6S)-trans-α-irone 
• 124988-45-0 (-)-(1R,5S)-2,5,6,6-tetramethylcyclohex-2-ene-1-carbaldehyde 

Relevant academic research and scientific papers

Enantioselective divergent synthesis of (-)-cis-a- And (-)-cis-g-irone by using wilkinson's catalyst

A simple, efficient synthesis is reported for (-)-cis-a-and (-)-cis-g-irone, two precious constituents of iris oils, in ≥99% diastereomeric and enantioselective ratios. The two routes diverge from a common intermediate prepared from (-)-epoxygeraniol. Of general interest in this approach is the installation of the enone moiety of irones through a NHC-AuI-catalyzed Meyer-Schuster-like rearrangement of a propargylic benzoate and the use of Wilkinson's catalyst for the stereoselective hydrogenation of a prostereogenic exocyclic double bond to secure the critical cis stereochemistry of the alkyl groups at C2 and C6 of the irones. The stereochemical aspects of this reaction are rationally supported by DFT calculation of the conformers of the substrates undergoing the hydrogenation and by a modeling study of the geometry of the rhodium ν2 complexes involved in the diastereodifferentiation of the double bond faces. Thus, computational investigation of the ν2 intermediates formed in the catalytic cycle of prostereogenic alkene hydrogenation by using Wilkinson's catalyst could be highly predictive of the stereochemistry of the products.

14. Preparation and Absolute Configuration of Some Iris Essential Oil Constituents of the 5-Methylsafranic-Acid Series

The β-dienoate (+)-(5S)-13a (86percent ee; meaning of α and β as in α- and β-irone, resp.) was obtained from (-)-(5S)-9a via acid-catalyzed dehydration of the diastereomer mixture of allylic tertiary alcohols (+)-(1S,5S)-15/(+)-(1R,5S)-15 (Scheme 3).Prolo

Preparation of Optically Active Flowery and Woody-Like Odorant Ketones via Corey-Chaykovsky Oxiranylation: Irones and Analogues

α-, β-, and γ-Irones and analogues have been prepared from optically active (+)-1, (+)-6a,b, and (+)-17, via a Corey-Chaykovsky oxiranylation (Me2S, Me2SO4, Me2SO, NaOH) followed by isomerisation (SnCl4 or MgBr2). (+)-Dihydrocyclocitral (19a), obtained from (-)-citronellal, and analogue (+)-19b, were condensed with various ketones to afford (+)-21a-f, and after hydrogenation (+)-22a-f.A mild oxidative degradation of aldehydes (+)-trans- and (-)-cis-8a,b to ketones (-)-16a,b, as well as olfactive evaluations, 13C-NMR assignments, and absolute configurations of the intermediate epoxides, aldehydes, and alcohols are presented.