One-step, enantiospecific transformation of cyclic, five-membered-1,2-diols into their respective 1,2-bis(phenylsulfanyl) derivatives

The enantiomeric cyclic, five-membered vic-diols reacted with (PhS)(2)/Bu3P in benzene at 80 degreesC giving the corresponding bis(phenylsulfanyl) derivatives (42-74%) with complete inversion of configuration at both stereogenic centers. Similar reaction conditions were also Successfully used for th...

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Bibliographic Details
Published inSynlett no. 11; pp. 1615 - 1618
Main Authors Skarzewski, J, Gupta, A, Wojaczynska, E, Siedlecka, R
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 02.09.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SULFOXIDES
diols
LIGANDS
ONE-POT
stereoselective synthesis
Mitsunobu reaction
thioethers
COMPLEXES
REACTIVITY
SULFUR
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Summary:The enantiomeric cyclic, five-membered vic-diols reacted with (PhS)(2)/Bu3P in benzene at 80 degreesC giving the corresponding bis(phenylsulfanyl) derivatives (42-74%) with complete inversion of configuration at both stereogenic centers. Similar reaction conditions were also Successfully used for the enantiospecific transformation of a single hydroxy group into the respective enantiomeric thioether function. For other vic-diols the neighboring group participation hampered the stereoselectivity of the double substitution.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2003-41015