153080-59-2

Upstream product

• 20229-41-8 l-menthyl phenylglyoxylate 
• 72793-38-5 2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-carbaldehyde 
• 87769-48-0 2,2-dimethyl-4H-1,3-dioxin-4-one 

Downstream Products

• 153080-61-6 l-menthyl (2R,6R)-4-oxo-2,6-diphenyl-1,3-dioxane-2-carboxylate 
• 153080-60-5 l-menthyl (2R,6S)-6-methyl-4-oxo-2-phenyl-1,3-dioxane-2-carboxylate 

Relevant academic research and scientific papers

l-Menthyl (R)-2-phenyl-4-oxo-1,3-dioxine-2-carboxylate: Diastereofacial selectivity for conjugate addition and its explanation

l-Menthyl (R)- and (S)-2-phenyl-4-oxo-1,3-dioxine-2-carboxylates are synthesized from l-menthyl phenylglyoxylate by reacting with formylketene followed by fractional crystallization. Conjugate addition to the (R)-2-phenyl-4-oxo-1,3-dioxine-2-carboxylate by RMgBr/CuI has revealed that the reagent attacks from the phenyl side which takes the quasi-equatorial orientation in the sofa comformation of the dioxinone ring with complete diastereoselection. This finding is contrast to the reverse diastereoselectivity in the same reaction of 2-tert-butyl-6-methyl-1,3-dioxin-4-one and its 2-methyl derivative. A possible reason to account for this difference is proposed.