135735-06-7

Upstream product

• 112968-75-9 (5R)-(L-menthyloxy)-2(5H)-furanone 
• 121-69-7 N,N-dimethyl-aniline 
• 2216-51-5 (-)-menthol 
• 122079-41-8 (5S)-(D-menthyloxy)-2(5H)-furanone 
• 86-56-6 N,N-dimethyl-1-naphthalenamine 
• 112968-75-9 (+)-(5S)-5-((+)-menthyl)oxy-2<5H>-furanone 
• 4096-21-3 N-phenylpyrrolidine 

Downstream Products

• 1196791-31-7 (3S,5R)-3-[(1S,3Z)-1-hydroxy-5-(6-methoxy-2H-1,3-benzodioxol-4-yl)-4-methylpent-3-en-1-yl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}dihydrofuran-2(3H)-one 
• 1196791-30-6 (3R,5R)-3-[(1S,3Z)-1-hydroxy-5-(6-methoxy-2H-1,3-benzodioxol-4-yl)-4-methylpent-3-en-1-yl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}dihydrofuran-2(3H)-one 
• 1196791-22-6 (3R,5R)-3-[(1R,3Z)-1-hydroxy-5-(6-methoxy-2H-1,3-benzodioxol-4-yl)-4-methylpent-3-en-1-yl]-5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}dihydrofuran-2(3H)-one 
• 176774-61-1 (3S,5S)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-3-propyl-dihydro-furan-2-one 
• 176774-60-0 (3S,5S)-3-Ethyl-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-dihydro-furan-2-one 
• 1365841-26-4 (7R,7aS)-1-benzyl-7-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-1H,2H,3H,5H,7H,7aH-furo[3,4-b]pyridin-5-one 
• 1365841-19-5 (7R,7aS)-1-benzyl-7-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)-cyclohexyl]oxy}-1H,2H,3H,5H,7H,7aH-furo[3,4-b]pyridin-5-one 
• 1365840-73-8 (3S,5R)-5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-oxy}-3-(phenylselanyl)oxolan-2-one 
• 1365840-74-9 (3S,5R)-5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]-oxy}-3-(phenylselanyl)oxolan-2-one 
• 176650-16-1 (3R,5R)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-3-propyl-dihydro-furan-2-one 
• 176650-15-0 (3R,5R)-3-Ethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-dihydro-furan-2-one 

Relevant academic research and scientific papers

Photochemical electron transfer mediated addition of naphthylamine derivatives to electron-deficient alkenes

Using photochemical electron transfer, N,N-dimethylnaphthylamine derivatives are added to α,β-unsaturated carboxylates. The addition takes place exclusively in the α-position of electron-deficient alkenes and mainly in the 4-position of N,N-dimethylnaphthalen-1-amine. A minor regioisomer results from the addition in the 5-position of this naphthylamine. A physicochemical study reveals that the fluorescence quenching of N,N-dimethylnaphthalen-1-amine is diffusion-controlled and that the back electron transfer is highly efficient. Therefore no transformation is observed at lower concentrations. To overcome this limitation and to induce an efficient transformation, minor amounts of water or another proton donor as well as an excess of the naphthylamine derivative are necessary. A mechanism involving a contact radical ion pair is discussed. Isotopic labeling experiments reveal that no hydrogen is directly transferred between the substrates. The hydrogen transfer to the furanone moiety observed in the overall reaction therefore results from an exchange with the reaction medium. An electrophilic oxoallyl radical generated from the furanone reacts with the naphthylamine used in excess. Concerning some mechanistic details, the reaction is compared with radical and electrophilic aromatic substitutions. The transformation was carried out with a variety of electron-deficient alkenes. Sterically hindered furanone derivatives are less reactive under standard conditions. In a first experiment, such a compound was transformed using heterogeneous electron transfer photocatalysis with TiO2.

Diastereoselective radical tandem addition-cyclization reactions of aromatic tertiary amines by semiconductor-sensitized photochemical electron transfer

The diastereoselective radical tandem addition-cyclization reaction of N,N-dimethylaniline (2) with menthyloxyfuranone 1 was initiated by photochemically induced electron transfer using inorganic semiconductors (TiO2, ZnS, SiC and SnO2) as sensitizers. The rearomatization step, which also causes the partial reduction of 1, was studied by isotopic labeling experiments using deuterated derivatives of 2. The influence of the semiconductor surface on these processes has been characterized and compared with the results obtained under homogeneous conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Diastereoselective tandem addition-cyclization reactions of unsaturated tertiary amines initiated by photochemical electron transfer (PET)

Polycyclic molecules and tetrahydroquinoleines were obtained in a tandem reaction involving the diastereoselective addition of α-aminoalkyl radicals to (5R)-5-menthyloxy-2[5H]-furanone 1. The facial diastereoselectivity on 1 is ≥90%. The α-aminoalkyl radicals were produced from tertiary amines by photochemical-induced electron transfer. When N, N-dialkylanilines 19 were used as starting tertiary amines, a rearomatization step was involved and important side reactions of 1 were observed. A mechanistic study involving isotopic labeling of the starting amine indicated that the byproducts resulted from reduction of I during the rearomatization process. An efficient optimization of the reaction was obtained by simply adding acetone or cyclopentanone as mild oxidants to the reaction mixture. The side products resulting from reduction of the furanone 1 were completely suppressed under these conditions, and the yields of the tetrahydroquinolines 21ai, 22a-f, and 26g-i were doubled.

Stereoselective radical-tandem reaction of aniline derivatives with (5R)-5-menthyloxy-2,5-dihydrofuran-2-one initiated by photochemical induced electron transfer

The radical tandem reaction of simple alkyl derivatives of aniline to a chiral furanone can be carried out stereoselectively in high yields; the furanone is also involved as oxidant in a rearomatisation process (formation of byproducts) where it can be re

Enantioselective synthesis of (R)- and (S)-2-alkyl-1,4-butanediols via enantiomerically pure 3-alkyl-5-(menthyloxy)butyrolactones

A general and practical synthesis of optically pure (R)- and (S)-2-ethyl, 2-propyl and 2-isopropyl-1,4-butanediols, 9a-c, has been accomplished from optically pure 5-(menthyloxy)butenolides in five steps in good yields.