- From enantiopure hydroxyaldehydes to complex heterocyclic scaffolds: Development of domino Petasis/diels-alder and cross-metathesis/Michael addition reactions
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One-step assembly of hexahydroisoindole scaffolds by a sequence that combines the Petasis (borono-Mannich) and Diels-Alder reactions is described. The unique selectivity observed experimentally was confirmed by quantum calculations. The current method is
- Cannillo, Alexandre,Norsikian, Stéphanie,Tran Huu Dau, Marie-Elise,Retailleau, Pascal,Iorga, Bogdan I.,Beau, Jean-Marie
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Read Online
- Fast synthesis of complex enantiopure heterocyclic scaffolds by a tandem sequence of simple transformations on α-hydroxyaldehydes
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Two tandems are faster than one! Properly sequenced reactions initiated by the Petasis aminoalcohol synthesis from boronic acids, diallylamine, and α-hydroxyaldehydes, including free aldoses, leads to rapid construction of complex enantiopure structures (see scheme). Copyright
- Cannillo, Alexandre,Norsikian, Stephanie,Retailleau, Pascal,Dau, Marie-Elise Tran Huu,Iorga, Bogdan I.,Beau, Jean-Marie
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supporting information
p. 9127 - 9131
(2013/07/26)
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- A novel approach to γ-hydroxy-α,β-unsaturated compounds
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A simple synthesis of (E)-alk-1-enyl mesylates from (E)-alk-1- enylphosphonates is reported. Construction of γ-hydroxy-α,β- unsaturated compounds was achieved by a two-step process involving dihydroxylation of the enol mesylates followed by HWE reaction of the resulting α-hydroxy aldehydes with activated methylphosphonates. Enantioselective synthesis of the title compounds is also reported.
- Krawczyk, Henryk,Wasek, Katarzyna,Kedzia, Jacek
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experimental part
p. 3299 - 3306
(2009/05/11)
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- Synthesis and properties of natural occurring α-hydroxyaldehydes
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A synthesis for aliphatic α-acetoxyaldehydes 18 is presented. These were converted to free aldehydes 9 by action of hog liver esterase. Aliphatic α-hydroxyaldehydes, recently recognized to be produced in the course of lipid-peroxidation of linoleic and other unsaturated fatty acids, are only stable for short time in solution. They react with amines to give Schiff bases. These are instable, but can be trapped after reduction with NaBH4 to the corresponding amines. Since α-hydroxyaldehydes are produced in the case of lipid peroxidation and were found to stimulate oxidative stress, Schiff base formation might be a physiological important process. α-Hydroxyaldehydes form under physiological conditions mercaptals by reaction with thiols.
- Kern, Werner,Spiteller, Gerhard
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p. 4347 - 4362
(2007/10/03)
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- Synthesis of Trimethylsilyloxy and Hydroxy Compounds from Carbanions and Bis(trimethylsilyl)peroxide.
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The reactions of bis(trimethylsilyl)peroxide with alkyl, vinyl, alkynyl, aromatic and heteroaromatic anions are described.Depending on the reaction conditions, the trimethylsilyloxy derivatives can be obtained alone or together with the corresponding trimethylsilyl derivatives, which is sometimes the major product.Enolates, generated using magnesium diisopropylamide give the corresponding hydroxycarbonyl compounds in good yields.An attempt to rationalise the above results is given, emphasising the wide use of bis(trimethylsilyl)peroxide in organic synthesis as an electrophilic hydroxylation reagent.
- Camici, Lucia,Dembech, Pasquale,Ricci, Alfredo,Seconi, Giancarlo,Taddei, Maurizio
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p. 4197 - 4206
(2007/10/02)
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- CARBON-CARBON BOND FORMING REACTION OF BIS(CHLOROMETHYL)SULFONE WITH CARBONYL COMPOUNDS: GENERAL ROUTE TO AROMATIC 2-CHLOROVINYL COMPOUNDS AND α-HYDROXYALDEHYDES
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Bis(chloromethyl)sulfone (1) has been proved to be a useful reagent for the synthesis of aromatic 2-chlorovinyl compounds (4) from aromatic aldehydes and of α-hydroxyaldehydes (5) from aliphatic carbonyl compounds with one carbon prolongation.The sec-butyllithium-aided reaction of 1 with aromatic aldehydes gives 1,3-oxathiolane-3,3-dioxides (2) which are converted to 4 in good yields by thermolysis.On the other hand, the sodium hydride-aided reaction of 1 with aliphatic carbonyl compounds is favorable to the formation of chloromethylsulfonyloxiranes (3).Titanium tetrachloride has been found to be an efficient reagent for hydrolysis of 3 to 5.
- Nagashima, Enkou,Suzuki, Kunio,Ishikawa, Motoaki,Sekiya, Minoru
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p. 1873 - 1879
(2007/10/02)
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