Resolution of (1,1′-binaphthalene)-2,2′-dithiol by enzyme catalysed hydrolysis of a racemic diacyl derivative

✍ Scribed by Matthias Kiefer; Rainer Vogel; Günter Helmchen; Bernhard Nuber

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 442 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)85237-6

✦ Synopsis

Both enantiomers of (l,l'-binaphthalene)-2,2'-dithiol (1) can be obtained with 98 % ee by enzymatic (cholesterol esterase) resolution of the corresponding $S'-dipentanoate. Absolute configuration and enantiomeric purity were determined by crystal structure and lH NMR analysis, respectively, of a diastereomeric derivative of 1.

Enantiomerically pure C2-symmetric binaphthalene derivatives are of interest as chiral ligands or building blocks for crown ethersl, host molecules2, liquid crystals 3, chiral phases for chromatography't and chiral auxiliaries~. Recently, we became interested in (l,l'-bmaphthalene)-2,2'-dithiol, which has so far been employed as crown ethe& and chiral auxiliaru6b.j.

A convenient method for the preparation of enantiomericahy pure (1,l '-bmaphthalene)-2,2'-dithiol on a gram scale was elusive until recently. Di Furia et al.7 have worked out a kinetic resolution of a corresponding thioether under Sharpless conditions. However, this method appears unsuitable for large scale preparation