100680-94-2

Upstream product

• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 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 
• 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) 
• 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 

Downstream Products

• 492-70-6 *,R^*)>-1,2-Diphenyl-1,2-ethandiol 
• 5928-66-5 (R)-benzoin 
• 100680-95-3 <2R-<2α(R^*),3aα,4α,7α,7aα>>-2-<(Octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-1,2-diphenylethanon 

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, V - The Synthesis of (S)-Benzoin from meso-Hydrobenzoin

An efficient synthesis of enantiomerically pure (S)-benzoin is described.In the key step, which is a selective acetal formation reaction, a compound of type 1 (e.g. -octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-ol (1a)) reacts with the hydroxy group at the (S)-centre of meso-hydrobenzoin (2) to yield 79percent of the acetal 3a.This compound is oxidized using N-chlorosuccinimide/dimethyl sulfide to yield the ketone 4, from which enantiomerically pure 5 is obtained by treatment with acid.The selectivity observed in acetal formation is discussed.