134642-18-5Relevant academic research and scientific papers
Baylis-Hillman chemistry: synthesis of cis- and trans-α-methylene-γ-lactones
Kabalka, George W.,Venkataiah, Bollu,Chen, Chunlan
, p. 4187 - 4189 (2006)
syn-Homoallylic alcohols prepared from Baylis-Hillman adducts react with CBr4/PPh3 to give trans-α-methylene-γ-lactones. Notably, the same alcohols yield the cis-α-methylene-γ-lactones in the presence of traces of p-toluenesulfonic a
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
supporting information, 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
, 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
Tailored α-methylene-γ-butyrolactones and their effects on growth suppression in pancreatic carcinoma cells
Ramachandran, P. Veeraraghavan,Pratihar, Debarshi,Nair, Hari Narayanan G.,Walters, Matthew,Smith, Sadie,Yip-Schneider, Michele T.,Wu, Huangbing,Schmidt, C. Max
supporting information; experimental part, p. 6620 - 6623 (2010/12/19)
A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) were synthesized via allylboration and screened against three human pancreatic cancer cell lines (Panc-1, MIA PaCa-2, and BxPC-3). This systematic study established a discernible relationsh
Control of stereochemistry: A general synthesis of cis- or trans-β,γ-disubstituted-γ-butyrolactones following Z-crotylboration
Ramachandran, P. Veeraraghavan,Pratihar, Debarshi,Biswas, Debanjan
, p. 3877 - 3879 (2007/10/03)
A general and practical procedure for the highly diastereoselective preparation of either the cis- or trans-β,γ-disubstituted-γ- butyrolactones by appropriate choice of Lewis or Bronsted acid catalysts during crotylboration or lactonization is reported. T
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.
