103548-00-1Relevant academic research and scientific papers
Butyrolactone synthesis via polar radical crossover cycloaddition reactions: Diastereoselective syntheses of methylenolactocin and protolichesterinic acid
Zeller, Mary A.,Riener, Michelle,Nicewicz, David A.
, p. 4810 - 4813 (2014)
A direct catalytic synthesis of γ-butyrolactones from simple alkene and unsaturated acid starting materials is reported. The catalytic system consists of the Fukuzumi acridinium photooxidant and substoichiometric quantities of a redox-active cocatalyst. Oxidizable alkenes such as styrenes and trisubstituted aliphatic alkenes are cyclized with unsaturated acids via polar radical crossover cycloaddition (PRCC) reactions. This method has been applied to the diastereoselective total synthesis of methylenolactocin and protolichesterinic acid.
Strain-Driven Dyotropic Rearrangement: A Unified Ring-Expansion Approach to α-Methylene-γ-butyrolactones
Lei, Xiaoqiang,Li, Yuanhe,Lai, Yang,Hu, Shengkun,Qi, Chen,Wang, Gelin,Tang, Yefeng
, p. 4221 - 4230 (2020/12/22)
An unprecedented strain-driven dyotropic rearrangement of α-methylene-β-lactones has been realized, which enables the efficient access of a wide range of α-methylene-γ-butyrolactones displaying remarkable structural diversity. Several appealing features of the reaction, including excellent efficiency, high stereospecificity, predictable chemoselectivity and broad substrate scope, render it a powerful tool for the synthesis of MBL-containing molecules of either natural or synthetic origin. Both experimental and computational evidences suggest that the new variant of dyotropic rearrangements proceed in a dualistic pattern: while an asynchronous concerted mechanism most likely accounts for the reactions featuring hydrogen migration, a stepwise process involving a phenonium ion intermediate is favored in the cases of aryl migration. The great synthetic potential of the title reaction is exemplified by its application to the efficient construction of several natural products and relevant scaffolds.
An efficient synthesis of α-methylene-β-butyrolactones from Baylis-Hillman adducts via an In-mediated Barbier reaction and stereoselective lactonization under MeSO2Cl/Et3N conditions
Park, Bo Ram,Kim, Ko Hoon,Kim, Jae Nyoung
scheme or table, p. 6568 - 6571 (2011/03/17)
An efficient synthesis of trans-α-methylene-β-butyrolactones is disclosed from syn-homoallylic alcohols via the intramolecular mesylate displacement reaction promoted by nearby ester group under the influence of MsCl/Et3N. syn-Homoallylic alcoh
Reactivite d'organozinciques allyliques β-fonctionnels γ-substitues. Preparation d'α-methylene γ-butyrolactones β- et γ-substituees
Lambert, Francois,Kirschleger, Bernard,Villieras, Jean
, p. 71 - 86 (2007/10/02)
Stable organozinc compounds derived from alkyl 3-alkyl 2-(bromomethyl) propenoates reacted with ketones and aldehydes to give α-methylene γ-butyrolactones in excellent yields.Different reaction parameters were studied and some transition states were proposed.
SYNTHESIS OF α-METHYLENE-γ-LACTONES VIA Cr AND Sn COMPLEXES OF β-CARBETHOXY AND β-NITRILE ALLYL BROMIDES
Drewes, S. E.,Hoole, R. F. A.
, p. 1067 - 1074 (2007/10/02)
The synthesis of some α-methylene-γ-lactones employing allylic Cr and Sn complexes is described.
