Stereospecific synthesis of P-epimeric (Rp1, Rp2)-bis-[O-l-menthylphenylphosphonothionyl] diselenide. A new variant of the stereoselective Staudinger reaction
✍ Scribed by Andrzej Łopusiński; Leszek Łuczak; Jan Michalski
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- English
- Weight
- 524 KB
- Volume
- 6
- Category
- Article
- ISSN
- 1042-7163
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✦ Synopsis
A n efficient procedure is described that leads to pure (SJ-0-1-menthylphenylthiophosphinate. The absolute configuration of this diastereomer was assigned by chemical correlation and confirmed by X-ray crystallography. The reaction of the isomer with phenyl azide, leading to amidate, is a new variant of the stereoselective Staudinger reaction. Addition of elemental selenium to the ( Sp)-thiophosphinate led to diastereomeric O-l-menthylphenylselenophosphonothioic acid, which was finally oxidized to the diastereomeric (Rpl ,Rp2)-bis-[0-1-menthylphenylphosphonothionyl] diselenide. The diselenide structure was unambiguously confirmed by 31P NMR spectroscopy.