- Chemoselective synthesis of β-ketophosphonates using lithiated α-(trimethylsilyl)methylphosphonate
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A highly chemoselective synthesis of β-ketophosphonates from pentafluorophenyl esters and lithiated methyl α-(trimethylsilyl)methylphosphonate has been developed. This mild lithiated phosphonate reagent allows the synthesis of functionalized β-ketophosphonates in the presence of unactivated esters with high yields. This method has been compared with the standard lithiated methylphosphonate reagent.
- Specklin, Simon,Cossy, Janine
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p. 3302 - 3308
(2015/03/30)
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- Convenient synthesis of 1-(Trimethylsilyl)-and 1-(Trimethylstannyl) vinylphosphonates
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(Equation present) Dimethyl 1,1-bis(trimethylsilyl)methylphosphonate and dimethyl 1-(trimethylsilyl)-1-(trimethylstannyl)methylphosphonate were succeeded to react with aromatic aldehydes in the presence of methyl benzoate as additive to give the correspon
- Okada, Yoshiharu,Maruyama, Tomohiro,Tamura, Shin-Ichi,Kameoka, Hirohito,Masuda, Satoshi,Tokuda, Yuichiro,Sakai, Junya,Nomura, Masato
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p. 778 - 790
(2014/07/08)
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- Fluoride Ion-Induced Horner-Emmons Reaction of α-Silylalkylphosphonic Derivatives with Carbonyl Compounds
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Dimethyl α-trimethylsilylbenzylphosphonate was allowed to react with carbonyl compounds in the presence of fluoride ion to give the corresponding olefins in fairly good yields.Use of CsF in tetrahydrofuran gave the best result.On the other hand, dimethyl trimethylsilylmethylphosphonate was allowed to react similarly with benzophenone to afford 1,1-diphenylethylene, dimethyl methylphosphonate, and dimethyl 2,2-diphenylethenylphosphonate.A similar result was obtained by using O,O-diethyl trimethylsilylmethylphophonothioate.But, reaction of trimethylsilylmethylphosphonic bis(diethylamide) afforded only the protodesilylation product.
- Kawashima, Takayuki,Ishii, Takafumi,Inamoto, Naoki
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p. 1831 - 1838
(2007/10/02)
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- A One Step Generation of α-Lithiotrimethylsilylalkanephosphonates. A New Preparative Route to Dialkyl 1-(Trimethylsilyl)alkanephosphonates and Vinylphosphonates
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Chlorotrimethylsilane phosphonoalkylation in the presence of lithium diisopropylamide (LDA) in excess leads to the generation of an α-silyl α-phosphonyl carbanion which can be protonated, alkylated or converted into vinylphosphonates.
- Aboujaoude, Elie Elia,Lietje, Stephane,Collignon, Noel,Teulade, Marie Paule,Savignac, Philippe
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p. 934 - 937
(2007/10/02)
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