220972-46-3

Upstream product

• 370874-78-5 5-⁽¹⁾-menthyloxy-2(5H)-furanone 
• 2216-51-5 (-)-menthol 
• 40981-57-5 3-bromo-5-methoxyfuran-2(5H)-one 

Downstream Products

• 646066-05-9 (3aR,4R,6aS)-4-(1-menthyloxy)-3-methyl-3a,6a-dihydrofuro[3,4-d]isoxazol-6-(4H)-one N-oxide 
• 220972-39-4 5-(R)-<(1R,2S,5R)-(-)-menthyloxy>-3-bromo-2(5H)-furanone 

Relevant academic research and scientific papers

Synthesis of enantiomerically pure spiro-cyclopropane derivatives containing multichiral centers

A novel chiral source, 5-(R)-[(1R,2S,5R)-(-)-menthyloxy]-3-bromo-2(5H)- furanone (5a), was obtained in 46% yield with d.e.≥98% from the epimeric mixture of 5-(1-menthyloxy)-3-bromo-2(5H)-furanone (Sa+5b) obtained via the bromination of an epimeric mixture

MIRC reactions of 2-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized anions. Preparation of homochiral bicyclic γ-butyrolactones

Homochiral (5R)-4-bromo-5-(l-menthyloxy)furan-2(5H)-one with stabilized carbanions (from nitroalkanes, malononitrile and ethyl acetoacetate) afforded enantiopure bicyclic compounds in good yield (70-90%). 3- Oxabicyclic[3.1.0]hexan-2-one derivatives were obtained with nitromethane and malonic acid derivatives. However, dihydrofuro[3,4-d]isoxazol-6-one and dihydrofuro[3,4-b]furan-6(4H)-one derivatives were obtained from nitroethane and ethyl acetoacetate, respectively.

A valuable synthetic route to spiro-cyclopropane derivatives containing multiple stereogenic centers

The unusual, functionalized spiro-cyclopropane derivatives containing four stereogenic centers 8a-8f were obtained in good yields with d.e. ≥98% via tandem double Michael addition/internal nucleophilic substitution of the novel chiral synthon, 5-l-menthyl