Asymmetric oxidation of thioethers. Optical resolution of [1,1′-binaphthalene]-2,2′-dithiol
✍ Scribed by Fulvio Di Furia; Giulia Licini; Giorgio Modena; Ottorino De Lucchi
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 159 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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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 dia
## The title compound was found to exhibit confortnaGona1 polymorphism which greatly injluenced the eficiency of the thermorearrangement to 2,2'-bis-S-(N,N-dbnethylthiocarbamato)-lJ'-bi~hthalene. Recognition of this phenomenon has allowed a reproducible synthesis of I,l'-bbtaphthalene-2.2'-dithiol.
The synthesis and resolution of 3,3%-bis(benzyloxy)-1,1%-binaphthalene-2,2%-diol 1 is described. A diastereomeric mixture of 7 (derived from (±)-1 and Boc-Ala-OH) was separated using crystallization and column chromatography.