Organocatalytic Enantioselective Selenosulfonylation of a C–C Double Bond To Form Two Stereogenic Centers in an Aqueous Medium

Organocatalytic selenosulfonylation of the C–C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectiviti...

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Veröffentlicht in:Journal of organic chemistry 2019-06, Vol.84 (12), p.8100-8111
Hauptverfasser: Chen, Zhili, Hu, Fangli, Huang, Shengli, Zhao, Zhengxing, Mao, Hui, Qin, Wenling
Format: Artikel
Sprache:eng
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Zusammenfassung:Organocatalytic selenosulfonylation of the C–C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00973