ChemInform Abstract: Diastereoselective Synthesis of Alliin by an Asymmetric Sulfur Oxidation.

✍ Scribed by I. KOCH; M. KEUSGEN

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 30 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199904184

✦ Synopsis

Diastereoselective Synthesis of Alliin by an Asymmetric Sulfur Oxidation.

-A facile synthesis of alliin (VI) based on the selective sulfur oxidation of protected S-allyl-L-cysteine (IV) using Sharpless reagent modified with equimolar amounts of water is reported. The chirality of the resulting sulfoxide can be controlled by choice of (-)-or (+)-diethyl tartrate as chiral auxiliary. Direct, cyclohexanone oxygenase catalyzed asymmetric oxidation of (S)-allyl-L-cysteine (III) provides a promising alternative way to alliin (VI). (yields in g). -(KOCH, I.;