Catalytic Enantioselective Claisen Rearrangements of O-Allyl β-Ketoesters
نویسندگان
چکیده
منابع مشابه
Photo-organocatalytic Enantioselective Perfluoroalkylation of β-Ketoesters
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 development of an enantioselective catalytic Claisen rearrangement1 remains an important yet elusive goal in chemical synthesis.2 With this objective in mind, we recently reported the acyl-Claisen rearrangement, a Lewis acid-catalyzed variant of the Bellus reaction3 that utilizes acid chlorides and allylic amines in the stereoselective synthesis of R,â-disubstituted-γ,δ-unsaturated carbonyl...
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The palladium-catalyzed reaction of (hetero)aryl bromides, chlorides, and nonaflates with α-allyl-β-ketoesters provides ready efficient access to functionalized 2,3-dihydrofurans. The reaction tolerates several useful substituents including chloro, fluoro, ether, ketone, ester, cyano, and nitro groups.
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A simple and efficient method is developed for the zinc catalyzed Claisen rearrangement of allyl aryl ethers to o-allyl phenols by stirring in an oil-bath at 55 °C in liquid phase. Moreover, zinc powder is re-cyclable up to six times use without much loss of significant activity. In addition to it, the products are obtained in good to excellent yields and are in a state of high purity. The stru...
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The doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangement of silylketene aminals derived from 5-substituted (3S,4E,alphaR)-1-benzyloxy-3-[N-acyl-N-(alpha-methylbenzyl)amino]pent-4-enes furnishes 2,3-disubstituted (R)-N-alpha-methylbenzyl (2S,3R,4E)-7-benzyloxyhept-4-enamides in >90% de under the "matched" control of both stereogenic centres. Rearrangement of the "mismatched" dia...
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ژورنال
عنوان ژورنال: Angewandte Chemie International Edition
سال: 2010
ISSN: 1433-7851
DOI: 10.1002/anie.201005183