ja210758n_si_003.cif (15.56 kB)
Phosphorothioic Acids and Related Compounds as Surrogates for H2SSynthesis of Chiral Tetrahydrothiophenes
dataset
posted on 2012-02-08, 00:00 authored by Forest
J. Robertson, Jimmy WuThe convenient preparation of chiral tetrahydrothiophenes
(THTs)
in high enantiopurity via phosphorothioic acids and related compounds
is reported. We consider these to be safer alternatives to the use
of H2S which is a highly toxic gas. Each of the THTs is
derived from a common intermediate, thereby greatly enhancing the
flexibility of the synthesis. The key transformation is a base-promoted,
intramolecular, carbon–sulfur bond-forming event. These reactions
are highly stereospecific as they operate through a double SN2 displacement mechanism. The methodology is amenable to a broad
array of functional groups and heterocycles. The tetrahydrothiophene
motif is important because it is present in a number of bioactive
natural products. They have also been utilized to promote various
asymmetric transformations including hydrogenation, epoxidation, cyclopropanation,
and aziridination reactions.
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motifcyclopropanationcompoundflexibilityintramolecularhydrogenationaziridinationacidalternativeSN 2 displacement mechanismtetrahydrothiophenemethodologyenantiopurityCompoundtransformationsynthesisChiralheterocycleSurrogateTHTPhosphorothioicstereospecificTetrahydrothiophenesTheH 2SepoxidationchiralbioactivearrayRelatedphosphorothioicpreparationAcid
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