A Sequential Indium-Mediated Aldehyde Allylation/Palladium-Catalyzed Cross-Coupling Reaction in the Synthesis of 2-Deoxy-β-C-Aryl Glycosides
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چکیده
منابع مشابه
A sequential indium-mediated aldehyde allylation/palladium-catalyzed cross-coupling reaction in the synthesis of 2-deoxy-beta-C-aryl glycosides.
Indium-mediated allylation of aldehydes with 2-chloro-3-iodopropene, followed by a palladium-catalyzed cross-coupling reaction with triarylindium reagents or arylboronic acids, leads to aryl-substituted homoallylic alcohols in good to excellent yields and diastereoselectivities. The products obtained from reactions conducted with d-glyceraldehyde acetonide can be transformed into 2-deoxy-beta-C...
متن کاملA review: synthesis of aryl C-glycosides via the heck coupling reaction.
In this article, we focus on the synthesis of aryl C-glycosides via Heck coupling. It is organized based on the type of structures used in the assembly of the C-glycosides (also called C-nucleosides) with the following subsections: pyrimidine C-nucleosides, purine C-nucleosides, and monocyclic, bicyclic, and tetracyclic C-nucleosides. The reagents and conditions used for conducting the Heck cou...
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A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-α-glycosides and 1,5-anhydro-2-C-aryl-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in aqueous media as a key step proceeds with complete regioselectivity at C-2 and enables access to 2-aryl-glycals with different configurations ...
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Palladium-catalyzed cross-coupling of aryl bromides with 2-aryl-1,3-dithianes is described. This methodology takes advantage of the relatively acidic benzylic proton of the dithiane, allowing it to act as a competent, polarity-reversed transmetalation reagent. This unique approach affords the ability to employ an orthogonal deprotection strategy, and practical routes to both diaryl ketones and ...
متن کاملDirect synthesis of ester-containing indium homoenolate and its application in palladium-catalyzed cross-coupling with aryl halide.
An efficient method for the synthesis of ester-containing indium homoenolate via a direct insertion of indium into β-halo ester in the presence of CuI/LiCl was described. The synthetic utility of the indium homoenolate was demonstrated by palladium-catalyzed cross-coupling with aryl halides in DMA with wide functional group compatibility.
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2009
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol901353f