213833-70-6

Upstream product

• 917-64-6 methyl magnesium iodide 
• 75-77-4 chloro-trimethyl-silane 
• 6485-40-1 (R)-Carvone 

Downstream Products

• 213833-72-8 (2R,3R,5R)-2-(1,3-dioxolan-2-yl)-5-isopropenyl-2,3-dimethylcyclohexanone 
• 254752-76-6 (3S,4S,5R,2'S,3a'R,6a'S)-3-[3-([1,3]dioxolan-2-yl)propyl]-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohexanone 
• 254752-75-5 (4S,5R,2'S,3a'R,6a'S)-3-[3-([1,3]dioxolan-2-yl)propyl]-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone 
• 254752-95-9 Methanesulfonic acid (1R,2R,3R,5R)-2-(2S,3aR,6aS)-hexahydro-furo[2,3-b]furan-2-yl-5-isopropenyl-2,3-dimethyl-cyclohexyl ester 
• 254752-73-3 (3R,4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethyl-3-(pent-4-enyl)cyclohexanone 
• 254752-92-6 (1R,2S,3R,2'S,3a'R,6a'S)-4-(4-(hexahydrofuro[2,3-b]furan-2'-yl)-2,3-dimethyl-5-oxocyclohexyl)butyraldehyde 
• 254752-71-1 (1R,2S,3R,5R,2'S,3a'R,6a'S)-2-(hexahydrofuro[2,3-b]furan-2'-yl)-5-isopropenyl-2,3-dimethyl-1-cyclohexanol 
• 254752-93-7 (5R,6R,2'S,3a'R,6a'S)-6-(hexahydrofuro[2,3-b]furan-2'-yl)-5,6-dimethylcyclohex-3-enone 
• 213833-79-5 (5R,6R,2'S,3a'R,6a'S)-6-(hexahydrofuro[2,3-b]furan-2'-yl)-5,6-dimethyl-3-(phenylsulfanyl)cyclohex-2-enone 
• 213833-80-8 (4S,5R,2'S,3a'R,6a'S)-4-(hexahydrofuro[2,3-b]furan-2'-yl)-4,5-dimethylcyclohex-2-enone 
• 213833-78-4 (5R,6R,2'S,3a'R,6a'S)-6-(hexahydrofuro[2,3-b]furan-2'-yl)-5,6-dimethylcyclohex-2-enone 
• 213833-77-3 (2R,3R,5R)-2-[(2R,3aS,6aR)-2,3,3a,4,5,6a-hexahydrofluoro[2,3-b]furan-2-yl]-5-isopropenyl-2,3-dimethylcyclohexanone 
• 213833-81-9 (2R,3R,5R,2'R,3a'S,6a'R)-2-(hexahydrofuro[2,3-b]furan-2'-yl)-5-isopropenyl-2,3-dimethylcyclohexanone 

Relevant academic research and scientific papers

Total synthesis of dihydroclerodin from (R)-(-)-carvone

The first total synthesis of the natural enantiomer of the insect- antifeedant dihydroclerodin (1) and lupulin C (40) has been achieved starting from (R)-(-)-carvone (2). In the applied strategy, the hexahydrofuro[2,3- b]furan moiety was introduced in an early stage of the synthesis: The correct configuration at C-9, C-11, C-13, and C-16 was established by application of a remarkably diastereoselective Mukaiyama reaction. The desired configuration at C-10 was obtained by catalytic reduction of the intermediate enone 21. After annulation of the second ring, the structural features at C-4, C-5, and C-6 were introduced. The successful finishing of the synthesis included a Chugaev elimination to give the exocyclic double bond at C-4 that is present in lupulin C. Oxidation of this double bond with m-CPBA afforded dihydroclerodin.

Enantioselective synthesis of highly functionalised cyclohexanones starting from R-(-)-carvone

Copper (1) catalysed conjugate addition of methylmagnesium iodide to R- (-)-carvone and trapping the enolate as its trimethylsilyl enol ether, followed by a trityl perchlorate (TrClO4) catalysed Mukaiyama-aldol reaction, is an efficient method

The Kharasch reaction revisited: CuX3Li2-catalyzed conjugate addition reactions of Grignard reagents

The conjugate addition of Grignard reagents RMgX to α,β-unsaturated ketones and esters is effectively catalyzed by soluble copper ate-complexes of the type CuX3Li2, e.g.CuI*2LiCl.In the presence of Me3SiCl the corresponding ketone enolsilanes are formed in high yield and selectivity.Diastereoselectivity in the case of chiral ketones is similar to that observed by using stoichiometric amounts of cuprates R2CuLi.Thus CuX3Li2-catalyzed 1,4-additions of Grignard reagents may be an industrially viable process.Keywords: Copper; Magnesium; Lithium; Silicon; Ketone; Enolsilanes