804548-76-3

Upstream product

• 112968-75-9 (5R)-(L-menthyloxy)-2(5H)-furanone 
• 804548-75-2 (3S,4R,5R)-4-butyl-3-(1-hydroxy-2-methylpropyl)-5-(l-menthyloxy)dihydrofuran-2-one 
• 804548-45-6 (4R,5R)-4-butyl-5-(l-menthyloxy)dihydro-2-furanone 

Relevant academic research and scientific papers

Conjugate addition of organocopper reagents to γ-alkoxybutenolides and application to the synthesis of non-racemic alkyl cyclopentenones

Simple organocopper reagents are shown to undergo anti-stereoselective 1,4-addition to menthyloxy-substituted lactone 1 in the presence of BF 3·OEt2; the Lewis acid causes partial epimerisation of the acetal centre after conjugate addition. Enolate alkylation of the adducts leads to di- and trisubstituted lactones that are converted, in favourable cases, into di- and trisubstituted cyclopentenones.