252267-55-3

Upstream product

• 252267-54-2 (1S,5S)-6-Oxo-2-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 252267-53-1 (1R,5S)-7,7-Dichloro-6-oxo-2-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 245674-44-6 2-Hydroxy-pyrrolidine-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 245674-34-4 2-Oxo-pyrrolidine-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 252267-56-4 Pyrrolidine-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 245674-48-0 2,3-Dihydro-pyrrole-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 245674-30-0 Imidazole-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Downstream Products

• 65253-04-5 (-)-8-phenylmenthol 
• 245674-30-0 Imidazole-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Relevant academic research and scientific papers

Diastereofacial selectivity in ketene [2+2] cycloaddition to endocyclic enecarbamates bearing a chiral auxiliary. Synthesis of the (-)-Geissman-Waiss lactone

The diastereofacial selectivity of enecarbamates bearing a chiral auxiliary was evaluated for the [2+2]cycloaddition with dichloroketenes. Diastereofacial selectivity ranged from zero (bornyl and menthyl) to 60% (Greene's auxiliary and 8-phenylmenthyl). Chromatography separation of the diastereomeric azacyclobutanones derived from the 8-phenylmenthyl enecarbamate permitted an enantiodivergent synthesis of the (-)-Geissman-Waiss lactone, a key intermediate in the synthesis of necine bases.