81978-44-1

Upstream product

• 98-85-1 1-Phenylethanol 
• 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 
• 87248-50-8 <2R,2'R-(2α,2'α,3aα,3a'α,4α,4'α,7α,7'α,7aα,7a'α)>-2,2'-Oxybis(2,3,3a,4,5,6,7,7a-octahydro-7,8,8-trimethyl-4,7-methanobenzofuran) 

Downstream Products

• 1445-91-6 (S)-1-phenylethanol 
• 81925-10-2 <2S-(2α,3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-2-methoxy-7,8,8-trimethyl-4,7-methanobenzofuran 
• 1517-69-7 (R)-1-phenylethanol 

Relevant academic research and scientific papers

Enantiomer-selektive Acetal-Bildung, ein Verfahren zur Reinherstellung bzw. Anreicherung von Enantiomeren

The enantiomeric selectivity of (3aS)-2α-hydroxy-7,8,8-trimethyloctahydro-4,7-methanobenzofuran (Mbf-OH), its O-methyl derivative (Mbf-OCH3), and its symmetrical oxide (Mbf-O-Mbf) makes possible the use of these reagents in the large-scale synthesis of the pure or enriched enantiomers of alkyl aryl carbinols without chromatographic separation of diastereoisomers.

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.