Efficient Asymmetric Synthesis of S,S-2-methylsulfanyl-2-methylsulfinyl-1-indanone

Derisvaldo Rosa Paiva, Roberto da Silva Gomes

Abstract


Diastereoselective synthesis of SS-2-methylsulfanyl-2-methylsulfinyl-1-indanol by reduction of SS-2-methylsulfanyl-2-methylsulfinyl-1-indanone optically enriched demonstrating to be highly efficiency using the sulfanyl group as asymmetric induction control agent during an addition reaction to carbonyl group.The 2-methylsulfinyl-1-indanone was obtained for the first time in one unique step without further oxidation steps.

The synthesis of SR, SS of 2-methylsulphinyl-1-indanone optically enriched in good yield and good enantiomeric excess determined by nuclear magnetic resonance technique employing the Kagan reagent as chiral shift agent.


Keywords


asymmetric synthesis; indanone; indanol; phase-transfer catalysis

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