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 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.9b00973 |