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Synthesis 2019; 51(23): 4417-4416
DOI: 10.1055/s-0039-1690034
DOI: 10.1055/s-0039-1690034
paper
Photochemical Deracemization of Chiral Sulfoxides Catalyzed by a Hydrogen-Bonding Xanthone Sensitizer
This project was supported by the Deutsche Forschungsgemeinschaft (Ba 1372-24/1) and by the TUM Graduate School.Further Information
Publication History
Received: 18 October 2019
Accepted: 21 October 2019
Publication Date:
04 November 2019 (online)
In memory of Dieter Enders
Abstract
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 λ = 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.
Key words
deracemization - enantioselective synthesis - homogeneous catalysis - photochemistry - sensitization - sulfoxidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690034.
- Supporting Information
Primary Data
- for this article are available online at https://doi.org/10.1055/s-0039-1690034 and can be cited using the following DOI: 10.4125/pd0109th.
- Primary Data
-
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Reviews:
Reviews on enantioselective sulfoxidation: