- Highly stereoselective coupling reaction of acrolein or vinyl ketone with aldehydes
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(formula presented) Treatment of acrolein with a TiCl4 - n-Bu4NI mixed reagent in the presence of 2 equiv of aldehydes provided 4-hydroxy-1,3-dioxane derivatives in good yields with high stereoselectivities. The use of vinyl ketones
- Uehira, Shigeki,Han, Zhenfu,Shinokubo, Hiroshi,Oshima, Koichiro
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- An Improved Protocol for the Morita-Baylis-Hillman Reaction Allows Unprecedented Broad Synthetic Scope
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The Morita-Baylis-Hillman (MBH) reaction has been stablished as an important C?C bond-forming transformation between carbonyl-containing compounds and activated olefins. However, the slow reaction rate usually observed with electron-rich electrophilic par
- Amarante, Giovanni W.,Camilo, Nilton S.,Carpanez, Arthur G.,Coelho, Fernando,Fernandes, Fábio S.,Lima, Samia R.,Rodrigues, Manoel T.,Santos, Hugo,Serafim, José Cláudio,Silva, Thiago S.,Zeoly, Lucas A.,de Oliveira, Aline S. B.
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supporting information
(2022/01/22)
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- α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita–Baylis–Hillman Reactions
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α-β-unsaturated acylsilanes are excellent substrates for Morita–Baylis–Hillman (MBH) reactions, affording the expected adducts in good to excellent yields. In these derivatives, as well as the corresponding acetates, the acylsilanes can be smoothly transf
- Marri, Gangababu,Justaud, Frédéric,Das, Saibal,Grée, René
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- Lithium perchlorate-accelerated Baylis-Hillman reactions
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The coupling of α, β-unsaturated carbonyl compounds with aldehydes (the Baylis-Hillman reaction) was accelerated in the presence of a catalytic amount of 1,4-diazabicyclo[2,2,2]octane (DABCO) and lithium perchlorate in ether. A preliminary kinetic study r
- Kawamura, Mikako,Kobayashi, Shu
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p. 1539 - 1542
(2007/10/03)
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- Aldol reaction of tert-butyldimethylsilyloxy allene with aromatic aldehydes, a direct route to acroleine aldol products
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tert-Butyldimethylsilyloxyallene reacts with aromatic aldehydes in the presence of BF3.Et2O to give corresponding aldol products.
- Kaur, Amarjit,Kaur, Gurmeet,Trehan, Sanjay
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p. 1048 - 1050
(2007/10/03)
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- On the Baylis-Hillman reaction of acrylate, acrylonitrile, and acrolein with some non-enolizable α-dicarbonyl compounds: synthesis of phytotoxic bipolaroxin models
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The Baylis-Hillman reaction of acrylonitrile, methyl acrylate, and acrolein with several cyclic α-dicarbonyl compounds was investigated.Whereas acrylonitrile reacted with most of these ketones, giving good yields of the expected 1'-cyanovinyl carbinols, t
- Strunz, George M.,Bethell, Richard,Sampson, Glen,White, Peter
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p. 1666 - 1674
(2007/10/02)
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- Aldolisation dirigee avec l'acroleine. Methode de synthese stereoselective de doubles liaisons trisubstituees fonctionnalisees. Application a la synthese du (+/-)-Z-chloronuciferal et du (+/-)-E-nuciferol
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To direct the aldolisation reaction in such a way that an aldehyde reacts upon the electrophilic carbonyl group of a ketone or of another aldehyde, it is necessary to mask the aldehyde and to transform it into a nucleophile.The present article presents an approach to this problem concerning unsaturated aldehydes and describes the condensation between the α-carbanion of acrolein and several carbonyl compounds. Aldol condensation at -70 degC, between 1,1-diethoxy-2-lithio-2-propene and several aldehydes leads to β-hydroxy-α-methylene acetals.These secondary allylic alcohols are stereoselectively transformed into trisubstituted functionalised olefinic compounds (Z-α-chlormethyl-α,β-unsaturated aldehydes and E-α-methyl-α,β-unsaturated primary alcohols). This method is illustrated by the syntheses of (+/-)-Z-chloronuciferal and (+/-)-E-nuciferol.
- Depezay, Jean-Claude,Merrer Le, Yves
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p. 306 - 312
(2007/10/02)
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