88335-92-6Relevant articles and documents
Photocatalyzed, β-Selective Hydrocarboxylation of α,β-Unsaturated Esters with CO2under Flow for β-Lactone Synthesis
Kang, Guowei,Romo, Daniel
, p. 1309 - 1315 (2021/02/01)
A photocatalyzed, β-selective hydrocarboxylation of α,β-unsaturated esters employing CO2 radical anion generated under flow conditions was developed. A range of substrates bearing a variety of functional groups were tolerated, demonstrating chemoselectivity. A series of quaternary carboxylic acids were obtained from sterically demanding β,β-disubstituted alkenes including those derived from natural products. Mechanistic studies support a Giese-type CO2 radical anion conjugate addition followed by hydrogen atom transfer from (TMS)3SiH as the principal reaction pathway. Finally, a telescoped process involving the described β-carboxylation followed by a α-bromination/β-lactonization sequence provides a strategy for β-lactone synthesis.
Remote conformational responses to enantiomeric excess in carboxylate-binding dynamic foldamers
Eccles, Natasha,Le Bailly, Bryden A.F.,Della Sala, Flavio,Vitórica-Yrezábal, I?igo J.,Clayden, Jonathan,Webb, Simon J.
supporting information, p. 9331 - 9334 (2019/08/08)
A crystallographically characterised zinc(ii)-capped foldamer can sense the enantiomeric excess of scalemic carboxylate solutions, including those produced by enantioselective organocatalysis, and can relay this input signal along the foldamer body to a remote glycinamide group, which then provides an NMR spectroscopic output.
Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
Xu, Lingjun,Han, Shuwen,Yan, Linjie,Wang, Haifeng,Peng, Haihui,Chen, Fener
supporting information, p. 309 - 317 (2018/02/19)
A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.
