Organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates of isatins
نویسندگان
چکیده
The investigation of a Lewis base catalyzed asymmetric allylic amination of Morita-Baylis-Hillman carbonates derived from isatins afforded an electrophilic pathway to access multifunctional oxindoles bearing a C3-quaternary stereocenter, provided with good to excellent enantioselectivity (up to 94% ee) and in high yields (up to 97%).
منابع مشابه
Asymmetric organocatalytic allylic alkylation of Reissert compounds: a facile access to chiral 1,1-disubstituted 1,2-dihydroisoquinolines.
The first asymmetric organocatalytic allylic alkylation of 1,2-dihydro-Reissert compounds and Morita-Baylis-Hillman (MBH) carbonates has been developed, which provided a novel protocol to construct enantioenriched functionalized 1,2-dihydroisoquinolines bearing vicinal quaternary and tertiary chiral centers at C-1 position (up to 94% ee, dr > 20 : 1).
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The peroxy-asymmetric allylic alkylation of hydroperoxyalkanes with Morita-Baylis-Hillman carbonates was catalysed by modified cinchona alkaloids (up to 93% ee), from which chiral alpha-methylene-beta-hydroxy esters could be efficiently derived.
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The first Lewis base-catalysed chemoselective asymmetric N-allylic alkylation of enamides with Morita-Baylis-Hillman carbonates has been developed, which affords multifunctional products in moderate to high enantioselectivity (up to 92% ee).
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The first organocatalytic asymmetric assembly of Morita-Baylis-Hillman carbonates of isatins and α-angelica lactone has been studied, affording multifunctional products containing two valuable pharmacophores and vicinal quaternary chiral centers in high stereoselectivity (up to 92% ee, dr >95:5).
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The highly enantioselective asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates with bis(phenylsulfonyl)methane is presented. The reaction is simply catalyzed by cinchona alkaloid derivatives affording the final alkylated products in good yields and enantioselectivities.
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