16822-06-3Relevant articles and documents
Indium mediated intramolecular carbocyclization in aqueous media. A facile and stereoselective synthesis of fused α-methylene-γ-butyrolactones
Bryan, Vernal J.,Chan, Tak-Hang
, p. 5341 - 5342 (1996)
Indium mediated intramolecular carbocyclization in aqueous media gave cis-fused α-methylene-γ-butyrolactones selectively in good yields.
Indirect Electroreductive Radical Cyclization of Halogeno Ethers using Nickel(II) Complexes as Electron-transfer Catalysts
Ozaki, Shigeko,Matsushita, Hidenori,Ohmori, Hidenobu
, p. 1120 - 1122 (1992)
Indirect electrochemical radical cyclization of halogeno ethers is achieved under mild conditions using nickel(II) complexes as electron-transfer catalysts.
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 (2018/05/07)
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.
α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B
Lloyd, Matthew G.,D'Acunto, Mariantonietta,Taylor, Richard J.K.,Unsworth, William P.
, p. 7107 - 7123 (2015/02/19)
Abstract A system for the synthesis of α-alkylidene-γ-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of α-diazo-α-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (±)-cedarmycins A and B is also described.
