Synthesis of Vinyl Boronates from Aldehydes by a Practical Boron–Wittig Reaction
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چکیده
منابع مشابه
Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides
Under the influence of a chiral palladium catalyst, 1,1-bis(pinacolboronate) esters undergo asymmetric cross-coupling with bromoalkenes to generate nonracemic allyl boronates with high levels of enantioselectivity. The so-formed allyl boronates may be oxidized with hydrogen peroxide to provide secondary allylic alcohols or with nitrosobenzene to furnish nonracemic tertiary allylic alcohols. Mec...
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Functionalized vinyl pinacol boronates suitable for Suzuki cross-coupling reactions are synthesized using ruthenium-catalyzed olefin cross-metathesis of 1-propenyl pinacol boronate and various alkenes, including functionalized and 1,1-disubstituted alkenes. The resultant boronate cross products are stereoselectively transformed into predominantly Z-vinyl bromides and E-vinyl iodides. The vinyl ...
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Due to its sensitivity to most synthetic reagents, it is typically necessary to introduce the boronic acid functional group just prior to its utilization. Overcoming this important limitation, we herein report that air- and chromatographically stable MIDA boronates are compatible with a wide range of common reagents which enables the multistep synthesis of complex boronic acid building blocks f...
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P-Silylated N,N-dialkyl amines (5) were easily synthesized in good to excellent yield from aldehydes (1), trimethylsilyldialkylamines (2), and trimethylsilylmethylmagnesium chloride (4) in the presence of 5 M lithium perchlorate solution in diethyl ether. The reaction Of (2) with aldehyde proceeded smoothly in the LiCI0 , to give the imimum salt (3). Addition of trimethylsilylmethylrnagnes...
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Condensation of 2H-benzo[g][1,2]oxasilocines with aromatic aldehydes in the presence of boron trifluoride affords mixtures of cis/trans 2-phenyl-3-vinylchromans with moderate yields. These can be transformed into homopterocarpans, a synthetic group of substances homologous to the natural isoflavonoid pterocarpans.
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2015
ISSN: 1523-7060,1523-7052
DOI: 10.1021/acs.orglett.5b00480