One-pot transformation of silyl enol ethers into 1,3-dienes: In situ generation of alkenyl nonaflates and subsequent heck reactions – scope and limitations was written by Lyapkalo, Ilya M.;Webel, Matthias;Reissig, Hans-Ulrich. And the article was included in European Journal of Organic Chemistry in 2002.Recommanded Product: 1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one This article mentions the following:
Palladium-catalyzed reactions between Me acrylate and the isolated alkenyl nonaflates proceed without difficulties, furnishing the desired 1,3-dienes in good yields. Starting nonaflates included 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonic acid 1-cyclopenten-1-yl ester, 1,1,2,2,3,3,4,4,4-Nonafluoro-1-butanesulfonic acid (1E)-1-nonenyl ester and 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonic acid 2-methyl-2-propenyl ester. The use of other alkenyl nonaflates and olefins in this Heck reaction was also examined The main purpose of this study was the development of an in situ generation of the required alkenyl nonaflates from the corresponding silyl enol ethers and their one-pot transformation into 1,3-dienes. Thus, the previously described fluoride-promoted exchange of the trimethylsilyl substituent of typical enol ethers was directly combined with the palladium-catalyzed coupling step. This sequence allowed the efficient transformation of a variety of silyl enol ethers 1 into highly substituted 1,3-dienes in a practical one-pot procedure. The scope and limitations, together with the chemo- and stereoselectivity, of this process are discussed. A particular intriguing example involves a one-pot synthesis of (1R,2R)-rel-4-[(trimethylsilyl)oxy]-4-Cyclohexene-1,2-dicarboxylic acid di-Me ester by means of a Diels-Alder reaction, subsequent nonaflation and a Heck reaction with tert-Bu acrylate, furnishing a highly functionalized 1,3-diene in good overall yield. In the experiment, the researchers used many compounds, for example, 1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (cas: 94594-91-9Recommanded Product: 1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one).
1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (cas: 94594-91-9) belongs to isothiazole derivatives. Isothiazole is a good solvent for many organic substances but should be used with caution because it is more toxic than pyridine. Various penicillins and cephalosporins having an isothiazole ring system have shown considerable antibacterial efficacy against Gram-positive and Gram-negative bacteria.Recommanded Product: 1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one
Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com