3727-50-2Relevant academic research and scientific papers
Synthesis of α-methylene-γ-lactone structure by cyclization of ω-formylallylsilane in water
Fukushima, Hiroki,Ikegami, Daisuke,Kuroda, Chiaki,Kobayashi, Kenichi
, p. 568 - 574 (2018)
Surfactant-type protonic acid-promoted intramolecular cyclization of functionalized allylsilanes was studied in water for the synthesis of α-methylene-γ-lactone compounds. ω-Formyl-β-(acetoxymethyl)allylsi-lane afforded carbocyclic compounds in good yields, while the cyclization product was not obtained from the corresponding β-ethoxycarbonyl derivative. It was found that (Z)-β-(acetoxymethyl)allylsilane predominantly afforded the cis-product, while (E)-β-(acetoxymethyl)allylsilane afforded both cis- and trans-products at a ratio of almost 1:1. The stereoselectivity of the cyclization reaction was almost the same as a protonic acid-promoted reaction in CH2Cl2 and was explained by an interaction between the C(Si)–C(alkene) bond and the carbonyl moiety. The cyclization products were converted to α-methylene-γ-lactone compounds.
PREPARATION AND SYNTHETIC APPLICATION OF 2-BROMOALLYLTRIMETHYLSILANE AS A 1-HYDROXYMETHYLVINYL ANION EQUIVALENT
Nishiyama, Hisao,Yokoyama, Hiroshi,Narimatsu, Shinzo,Itoh, Kenji
, p. 1267 - 1270 (2007/10/02)
The 1-trimethylsilylmethylvinyl group, as a 1-hydroxymethylvinyl equivalent, was readily introduced to epoxides with the corresponding Grignard reagent derived from 2-bromoallyltrimethylsilane.Obtained 2-(2-hydroxyethyl)-allylsilanes were converted to α-methylene-γ-lactones via diols.
