87248-60-0

Upstream product

• 81925-09-9 <2S-(2α,3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-ol 
• 618-36-0 rac-methylbenzylamine 

Downstream Products

• 82041-85-8 ((R)-1-Phenyl-ethyl)-((1R,2S,4S,6S,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yl)-amine 
• 740041-78-5 <2R-(2α(R*),3aβ,4β,7β,7aβ)>-2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-N-(1-phenylethyl)-4,7-methano-2-benzofuranamin 

Relevant academic research and scientific papers

Chiral Lactols, II. Racemate Separation and Enantioselective Acetalisation with the 2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl Protective Group

A simple method for the resolution of the chiral alcohols, cyanohydrins, thiols and amines rac-2a - f by the reaction with the chiral protective group 1a ( or 1b, respectively) is described.The diastereomeric derivatives 3a - f and 4a - f are separated by column chromatography or crystallisation.Subsequent methanolysis or hydrolysis, respectively, yields the enantiomers and the recovered protective group.With rac-2a - c preferential acetalisation of the (R)-enantiomers was observed.This phenomenon was investigated by modification of the protective group.Considerations on conformations of 3a point to an important role of the anomeric and exo-anomeric effect in this enantioselective reaction.