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Paper | Regular issue | Vol 60, No. 1, 2003, pp.47-56
Published online, 28th October, 2002
DOI: 10.3987/COM-02-9603
Phosphine-assisted Rearrangement of 4,5-Dihydroxy-1,2-dithianes to 4-Hydroxy-3-mercaptotetrahydrothiophenes

Sang Hyup Lee and Harold Kohn*

*Division of Medicinal Chemistry and Natural Products, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7360, U.S.A.


Treatment of 4,5-dihydroxy-1,2-dithianes with trialkylphosphines and triphenylphosphine under neutral and moderately basic conditions led to the efficient and stereospecific production of 4-hydroxy-3-mercaptotetrahydrothiophenes. The reaction is projected to proceed through three successive intramolecular rearrangements.