Organocatalytic peroxy-asymmetric allylic alkylation.
نویسندگان
چکیده
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.
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).
متن کاملOrganocatalytic chemoselective asymmetric N-allylic alkylation of enamides.
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).
متن کاملEnantioselective organocatalytic asymmetric allylic alkylation. Bis(phenylsulfonyl)methane addition to MBH carbonates.
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.
متن کاملEnantioselective desymmetrization of prochiral 1,3-dinitropropanes via organocatalytic allylic alkylation.
An enantioselective desymmetrization of prochiral 1,3-dinitropropanes has been developed which proceeds via enantiogroup differentiating organocatalytic allylic alkylation. Densely functionalized products with two vicinal stereocenters were obtained generally with good to excellent diastereoselectivity (up to >20 : 1 dr) and superb enantioselectivity (up to >99 : 1 er).
متن کاملOrganocatalytic enantioselective allylic alkylation of MBH carbonates with β-keto esters.
The highly stereoselective allylic alkylation of Morita-Baylis-Hillman carbonates with β-ketoesters catalysed by β-ICD is described. The corresponding products containing two adjacent quaternary and tertiary carbon centers were obtained in good yields with high diastereoselectivity (up to 10 : 1 dr) and enantioselectivity (up to 95% ee).
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 7 18 شماره
صفحات -
تاریخ انتشار 2009