Recent Advances in β-Lactone Chemistry

Pommier, Agnès; Pons, Jordi

doi:10.1055/s-1993-25878

Cited by 185 publications

(91 citation statements)

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“…6 This outcome is in sharp contrast to the thermolytic conditions (>60 ºC) typically required for decarboxylative [2+2]-cycloreversion of β-lactones (Scheme 3). 11 Reduced temperatures have traditionally only been achieved through radical decarboxylation. 12 Electron-neutral ( 2b ) and -poor ( 2c ) β-lactones are stable to Scheme 1 conditions; decarboxylation only occurs after heating in SiO 2 (Scheme 3), as previously observed.…”

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confidence: 99%

Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application

et al. 2015

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An unusual room temperature β-lactone decarboxylation facilitated a five-step enantioselective formal synthesis of the cyclopentane core of an estrogen receptor β-agonist. A computational study probed the underlying factors facilitating unprecedented, rapid decarboxylation. Aryl substitution promotes faster reaction in the retro-[2+2] as a result of conjugative stabilization with the forming olefin. Additionally, the configuration of the α-ester in these fused β-lactones leads to differential decarboxylation rates resulting in enantioselectivity.

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confidence: 99%

Functionalized cyclopentenes through a tandem NHC-catalyzed dynamic kinetic resolution and ambient temperature decarboxylation: mechanistic insight and synthetic application

et al. 2015

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“…Supplementary data (specific experimental procedures and 1 H and 13 C NMR spectra for 16a, 19a and 20a + 20b) associated with this article can be found, in the online version, at doi: 10 …”

Section: Supplementary Datamentioning

confidence: 99%

Indium-mediated Reformatsky reaction on lactones: preparation of 2-deoxy-2,2′-dimethyl-3-ulosonic acids

Soengas

2010

Tetrahedron Letters

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“…Decarboxylation of b-lactones is a stereospecific syn elimination [25,26]. Thus, the stereochemical assignments for lactones 21 and 22 follow from the respective alkene configurations.…”

Section: Ketene Formationmentioning

confidence: 99%