Journal
SYNTHESIS-STUTTGART
Volume 51, Issue 23, Pages 4417-4424Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690034
Keywords
deracemization; enantioselective synthesis; homogeneous catalysis; photochemistry; sensitization; sulfoxides
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Funding
- Deutsche Forschungsgemeinschaft [Ba 1372-24/1]
- TUM Graduate School
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Several chiral sulfoxides with a lactam hydrogen-bonding site were prepared and their photochemical behavior was studied in the presence of xanthone and thioxanthone sensitizers. While acyclic sulfoxides showed only decomposition, chiral benzothiazinone-1-oxides with a stereogenic sulfur atom underwent a stereomutation upon irradiation at lambda = 366 nm in the presence of catalytic quantities of a xanthone sensitizer. A chiral xanthone with a 1,5,7-trimethyl-3-azabicyclo-[3.3.1]nonan-2-one backbone was employed in catalytic quantities (5 mol%) to achieve a deracemization reaction of racemic benzothiazinone-1-oxides in acetonitrile solution. Five substrates could be successfully deracemized in good yields and with up to 55% ee .
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