128756-48-9Relevant academic research and scientific papers
Diastereoselective synthesis of trans-3,5-disubstituted dihydrofuran-2(3H)-ones via SmI2-mediated reductive coupling of 2-alkylacrylates of N,N-diisopropyl-2-hydroxybenzamide with aldehydes
Lai, Yecai,Sun, Lijie,Sit, Man Ki,Wang, Yan,Dai, Wei-Min
, p. 664 - 673 (2016)
Samarium(II) diiodide has been used to mediate reductive coupling reactions of aldehydes with a variety of substituted acrylates, in both achiral and chiral forms, for accessing substituted dihydrofuran-2(3H)-ones (γ-butyrolactones). Two major issues, concerning with self-dimerization of α-non-branched aliphatic aldehydes and low diastereoselectivity of the products, render limited application of the reductive coupling protocol in total synthesis of natural products. We report here on a novel type of substituted acrylates derived from the 2-amido arenols (HO-Aram) such as N,N-diisopropyl-2-hydroxybenzamide. The acrylates of HO-Aram enable: (a) preferential conjugate reduction of the acrylates than carbonyl reduction of aliphatic aldehydes, leading to diminished aldehyde self-dimerization; and (b) organization of an eight-membered ring among the amide carbonyl oxygen atom and samarium(III) to form a 7/8-bicyclic transition state, resulting in highly diastereoselective protonation of the samarium(III) enolate intermediate. Examples of synthesis of trans-3,5-disubstituted dihydrofuran-2(3H)-ones from 2-alkylacrylates of HO-Aram and aliphatic aldehydes are provided.
An expeditious enantioselective synthesis of γ-lactones
Chong,Mar
, p. 1981 - 1984 (2007/10/02)
α-Alkoxyorganolithium reagents react with α,β-unsaturated trimethylhydrazides to give γ-alkoxytrimethylhydrazides in moderate to good yields. Acid hydrolysis of the latter compounds yields γ-lactones. A short enantioselective route to (S)-hexanolide is described.
