111193-91-0Relevant academic research and scientific papers
A comparison of the Still-Gennari and Ando HWE-methodologies with α,β-unsaturated aldehydes; unexpected results with stannyl substituted systems
Franci, Xavier,Martina, Sébastien L.X.,McGrady, John E.,Webb, Michael R.,Donald, Craig,Taylor, Richard J.K.
, p. 7735 - 7740 (2003)
Still-Gennari reactions have been carried out on a range of E- and Z-3-substituted propenals. In all cases, with the exception of Z-3-stannyl systems, good Z-stereoselectivity was observed. By contrast, the Ando procedure gives reasonable Z-stereoselectivity with all systems studied, including those with a cis-disposed stannyl substituent.
Rasta resin-PPh3 and its use in chromatography-free wittig reactions
Leung, Peter Shu-Wai,Teng, Yan,Toy, Patrick H.
, p. 1997 - 2001 (2010)
Rasta resin-PPh3, a new heterogeneous polystyrene-based phosphine, has been synthesized and used in one-pot Wittig olefination reactions of aldehydes. In these reactions an excess of rasta resin-PPh3 was used for the in situ generation of the phosphorane reactant and allowed for isolation of a high yield of very pure alkene product after only filtration and solvent removal. The excellent results obtained in this study are attributed to the flexible nature of the rasta resin structure, which makes it less dependant upon swelling than other heterogeneous polystyrene materials previously used to support phosphine reagents in Wittig reactions. Georg Thieme Verlag Stuttgart.
Synthesis of α,β-Disubstituted Acrylates via Galat Reaction
Xavier, Tania,Condon, Sylvie,Pichon, Christophe,Le Gall, Erwan,Presset, Marc
supporting information, p. 6135 - 6139 (2019/08/28)
Galat reactions between aldehydes and substituted malonic acids half oxyester were found to be efficiently catalyzed by morpholine in refluxing toluene. This transformation allows the stereoselective synthesis of diverse α,β-disubstituted acrylates in moderate to good yields. This method constitutes an attractive alternative to existing methods in terms of scope and eco-compatibility.
Correlation of hydrolysis and desilylation of 2-[(trimethylsilyl)methyl] acrylate derivatives in aqueous alkali solutions
Kuroda, Chiaki,Sunakawa, Takeshi,Muguruma, Yuichi
scheme or table, p. 888 - 896 (2009/03/11)
Hydrolysis and desilylation reaction of 2-[(trimethylsilyl)methyl]acrylate (=2-[(trimethylsilyl)methyl] prop-2-enoate) derivatives were studied to evaluate the effect of the presence/absence of a further conjugating substituent (Schemes 3 and 4 and Tables 1 and 2). The substrates having a nonconjugating substituent at the acrylate moiety were stable to dilute alkali conditions, and afforded simple hydrolysis products under concentrated alkali conditions. In contrast, both hydrolysis and desilylation occurred from the substrates bearing conjugated substituents at the acrylate skeleton. The difference in reactivity can be explained in terms of the stabilization of the intermediate anion.
Reactivity of substituted and unsubstituted diphenylphosphonium diylides towards carbonic acids derivatives
Cristau,Taillefer
, p. 1507 - 1522 (2007/10/03)
In order to further delimit the scope of application of diphenylphosphonium diylides, their reactivity towards carbonic acid derivatives was investigated. Non-stabilized diylides react with ethyl carbonate to give new monoylide intermediates which lead, by in situ Wittig reaction with carbonyl compounds, to the synthesis of α,β-unsaturated esters or acids the double bond being di- or trisubstituted. The reaction proceeds in mild conditions and with high E stereoselectivity. Stabilized diylides are inactive towards carbonates but semi-stabilized diylides react with ethyl carbonate leading to the synthesis of non-functionalized alkenes instead of the α,β-unsaturated esters or acids.
STEREOCONTROLLED SYNTHESES OF STROBILURIN A AND ITS (9E)-ISOMER
Beautement, Kevin,Clough, John M.
, p. 475 - 478 (2007/10/02)
The (E,Z,E)-configuration (1) of the strobilurins has been confirmed by stereocontrolled synthesis.
