- Metal-free Bronsted acid catalyzed formal [3 + 3] annulation. Straightforward synthesis of dihydro-2H-chromenones, pyranones, and tetrahydroquinolinones
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(Chemical Equation Presented) Bronsted acids catalyze the addition of enolizable β-diketones, β-ketoesters, and vinylogous amides to α,β-unsaturated aldehydes to lead to substituted chromenones, pyranones, and tetrahydroquinolinones in good yields under mild reaction conditions via a formal [3 + 3] cycloaddition.
- Moreau, Julie,Hubert, Claudie,Batany, Jessika,Toupet, Loic,Roisnel, Thierry,Hurvois, Jean-Pierre,Renaudz, Jean-Luc
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supporting information; experimental part
p. 8963 - 8973
(2010/03/04)
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- Bronsted acid-catalyzed synthesis of pyrans via a formal [3+3] cycloaddition
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Bronsted acids catalyze the addition of enolizable ss-keto esters to α,ss-unsaturated aldehydes leading to substituted 2H-pyrans in good yields under mild conditions via a formal [3+3] cycloaddition.
- Hubert, Claudie,Moreau, Julie,Batany, Jessika,Duboc, Agathe,Hurvois, Jean-Pierre,Renaud, Jean-Luc
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supporting information; body text
p. 40 - 42
(2009/04/07)
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- A Lewis acid-catalyzed formal [3 + 3] cycloaddition of α,β- unsaturated aldehydes with 4-hydroxy-2-pyrone, diketones, and vinylogous esters
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A Lewis acid-catalyzed formal cycloaddition of α,β-unsaturated aldehydes with 6-methyl-4-hydroxy-2-pyrone, 1,3-diketones, and vinylogous silyl esters is described here.
- Kurdyumov, Aleksey V.,Lin, Nan,Hsung, Richard P.,Gullickson, Glen C.,Cole, Kevin P.,Sydorenko, Nadiya,Swidorski, Jacob J.
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p. 191 - 193
(2007/10/03)
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- A formal [3 + 3] cycloaddition reaction. Improved reactivity using α,β-unsaturated iminium salts and evidence for reversibility of 6π-electron electrocyclic ring closure of 1-oxatrienes
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A detailed account regarding a formal [3 + 3] cycloaddition method using 4-hydroxy-2-pyrones and 1,3-diketones is described here. This formal cycloaddition reaction or annulation reaction is synthetically useful for constructing 2H-pyranyl heterocycles. T
- Shen, Hong C.,Wang, Jiashi,Cole, Kevin P.,McLaughlin, Michael J.,Morgan, Christopher D.,Douglas, Christopher J.,Hsung, Richard P.,Coverdale, Heather A.,Gerasyuto, Aleksey I.,Hahn, Juliet M.,Liu, Jia,Sklenicka, Heather M.,Wei, Lin-Li,Zehnder, Luke R.,Zificsak, Craig A.
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p. 1729 - 1735
(2007/10/03)
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- The Reactivity of 4-Hydroxy-6-methyl-2-pyrone Towards Aliphatic Saturated and α,β-Unsaturated Aldehydes
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4-Hydroxy-6-methyl-2-pyrone (triacetic acid lactone) reacts at C-3 with 2-butenal and similar aldehydes by Michael addition.The nonisolated intermediates can undergo transformations in at least five different ways.On the contrary, reaction of the title py
- March, P. de,Moreno-Manas, M.,Casado, J.,Pleixats, R.,Roca, J. L.,Trius, A.
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