99685-54-8

Upstream product

• 2216-51-5 (-)-menthol 
• 542-92-7 cyclopenta-1,3-diene 
• 334947-54-5 (5S,S_S)-5-[(1R)-menthyloxy]-4-(phenylsulfinyl)furan-2(5H)-one 
• 157840-63-6 (5S)-4-phenylthio-5-(l-menthyloxy)furan-2-(5H)-one 
• 112968-75-9 (+)-(5S)-5-((+)-menthyl)oxy-2<5H>-furanone 
• 112968-75-9 (5R)-(L-menthyloxy)-2(5H)-furanone 
• 370874-78-5 5-⁽¹⁾-menthyloxy-2(5H)-furanone 

Downstream Products

• 129111-82-6 (2S,5R,6R)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-2-methyl-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 129111-85-9 (2S,5R,6R)-2-Ethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 
• 64550-47-6 (2S,6R)-4-Oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 

Relevant academic research and scientific papers

Stereoselectivity control in Diels-Alder reactions of 4-thiosubstituted 5-alkoxyfuranones: Synthesis and reactivity of enantiopure 4-sulfinyl and sulfonyl 5-(l-menthyloxy)furan-2(5H)-ones

The synthesis of enantiomerically pure (S)-4-phenylsulfinyl- and 4-phenylsulfonyl-(5S)-5-(l-menthyloxy)furan-2(5H)-ones 5a and 6 and (5R)-5-(l-menthyloxy)-4-phenylsulfonylfuran-2(5H)-one 8 and the study of their reactions with cyclopentadiene are described. The sulfur substituents at C-4 modify (sulfone 8, anti/syn = 78/22) and invert (sulfoxide 5a and sulfone 6, anti/syn≈27/73) the trend imposed by C-5 on the π-facial selectivity and the syn-adducts become the favoured ones. The endo or exo approach mode is favoured for anti (endo/exo ratio ranging between 26 and 5) or syn (exo/endo ratio ranging between 4.5 and 2.3) attack, respectively.

Asymmetric Diels-Alder Reactions of γ-Alkoxy-α-sulfinylbutenolides

The synthesis of the enantiomerically pure 6-ethoxy-3-p-tolylsulfinyl-2(5H)-furanones (2a and 2b) and the study of their behaviour as dienophiles in asymmetric Diels-Alder reactions with cyclopentadiene are reported.Depending on the reaction conditions, t

Asymmetric Diels-Alder Reactions with a Chiral Maleic Anhydride Analogue 5-(1-Menthyloxy)-2(5H)-furanone

5-(1-Menthyloxy)-2(5H)-furanone was used as a chiral dienophile in thermal asymmetric Diels-Alder reactions with several cyclic and acyclic dienes to give enantiomerically pure products.