Towards an asymmetric organocatalytic α-cyanation of β-ketoesters
نویسندگان
چکیده
منابع مشابه
Towards an asymmetric organocatalytic α-cyanation of β-ketoesters
This communication describes the first proof of concept for an asymmetric α-cyanation of β-ketoesters using a hypervalent iodine-based electrophilic cyanide-transfer reagent. A series of different organocatalysts has been investigated and it was found that the use of naturally occurring Cinchona alkaloids allows obtaining the target products in good yields and with moderate enantioselectivities...
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The visible-light-driven, phase-transfer-catalyzed, enantioselective perfluoroalkylation and trifluoromethylation of cyclic β-ketoesters is described. The photo-organocatalytic process, which occurs at ambient temperature and under visible light illumination, is triggered by the photochemical activity of in situ-generated electron donor-acceptor complexes, arising from the association of chiral...
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The 1,4-conjugate addition of nucleophiles to α,β-unsaturated carbonyl compounds represents one fundamental bond-forming reaction in organic synthesis. The development of effective organocatalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cycloenones constitutes an important research field and has been explored in recent...
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The first organocatalytic "anti-Michael" reaction of cyclic-beta-ketoesters to unsaturated double bonds is described in a highly asymmetric version leading to the synthesis of alpha,alpha'-disubstituted branched double bonds as optically active Baylis-Hillman-like adducts.
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We report the first catalytic asymmetric cyanation of N-Boc ketoimines, which enables highly enantioselective synthesis of oxindole based α-amino nitriles. An unprecedented tandem aza-Wittig/Strecker reaction is also developed, emerging as a promising strategy for the catalytic asymmetric cyanation of ketoimines formed in situ from achiral ketones.
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ژورنال
عنوان ژورنال: Tetrahedron Letters
سال: 2015
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2015.02.116