Asymmetric Synthesis of Remote Quaternary Centers by Copper-Catalyzed Desymmetrization: An Enantioselective Total Synthesis of (+)-Mesembrine.
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DOI: 10.1021/acs.orglett.8b02084
Abstract: Catalytic asymmetric syntheses of remote quaternary stereocenters have been developed by copper-catalyzed 1,4-hydrosilylation of γ,γ-disubstituted cyclohexadienones. A variety of cyclohexenones have been synthesized in good yield and excellent enantioselectivity. Versatile 2-silyloxy diene intermediates bearing γ,γ-disubstituted… read more here.
Keywords: synthesis mesembrine; total synthesis; remote quaternary; synthesis ... See more keywords
Distal Ionic Substrate–Catalyst Interactions Enable Long-Range Stereocontrol: Access to Remote Quaternary Stereocenters through a Desymmetrizing Suzuki–Miyaura Reaction
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DOI: 10.1021/jacs.1c12345
Abstract: Spatial distancing of a substrate’s reactive group and nonreactive catalyst-binding group from its pro-stereogenic element presents substantial hurdles in asymmetric catalysis. In this context, we report a desymmetrizing Suzuki–Miyaura reaction that establishes chirality at a… read more here.
Keywords: miyaura reaction; remote quaternary; catalyst; suzuki miyaura ... See more keywords