215321-43-0

Upstream product

• 79-37-8 oxalyl dichloride 
• 65253-04-5 (-)-8-phenylmenthol 

Downstream Products

• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 
• 212073-12-6 (-)-(1R)-8-phenylmenthyl (1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate 
• 212073-01-3 (-)-(1R)-8-phenylmenthyl (1R,3-exo)-2-benzyl-2-azabicyclo[2.2.1]heptane-3-carboxylate 
• 108794-12-3 <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl dihydroxyacetate 

Relevant academic research and scientific papers

An efficient method for preparation of chiral arylmenthol glyoxylates

Glyoxylates of three chiral alcohols were conveniently prepared by reaction of the alcohol with oxalyl chloride followed by reduction of the resulting alkoxy oxalyl chloride with tributyl- tin hydride. The products were isolated in 75-80% yield by straightforward flash chromatography.

The use of (-)-8-phenylisoneomenthol and (-)-8-phenylmenthol in the enantioselective synthesis of 3-functionalized 2-azabicyclo[2.2.1]heptane derivatives via aza-Diels-Alder reaction

The asymmetric aza-Diels-Alder reaction of the (1R)-8-phenylmenthyl or (1R)-8-phenylisoneomenthyl glyoxylate-derived N-benzylimine with cyclopentadiene resulted in the enantioselective synthesis of the corresponding pure [(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-ene]-3-carboxylates (80 or 69% yield, respectively). Reduction of these cycloadducts with LiAlH4 afforded pure (-)-[(1S,3-exo)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-yl]methanol. Furthermore, a reaction sequence based on Barbier-Wieland degradation of both (1S,3-exo)-adducts afforded pure (+)-(1R)-2-benzoyl-2-azabicyclo[2.2.1]heptan-3-one. In the course of the two transformation sequences referred, the chiral auxiliaries were recovered in a virtually quantitative way.