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Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives (CROSBI ID 221558)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Lemoine, H. ; Markovic, D. ; Deguin, B. Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives // Journal of organic chemistry, 79 (2014), 4358-4366. doi: 10.1021/jo500220h

Podaci o odgovornosti

Lemoine, H. ; Markovic, D. ; Deguin, B.

engleski

Mild and Chemoselective Lactone Ring-Opening with (TMS)ONa. Mechanistic Studies and Application to Sweroside Derivatives

Mild and chemoselective opening of lactones with sodium trimethylsilanolate in high yields and aprotic solvents is described. Kinetic studies demonstrate that the B(Ac)2 mechanistic pathway is followed. Nucleophilic attack of silanolate onto the carbonyl of the lactone moiety is the rate-determining step. NaOH present as an impurity accelerates the reaction. The method was further applied to the base-sensitive and stable lactones derived from highly functionalized iridoid derivatives.

Lactones (TMS)ONa; Mechanistic Studies; Sweroside;

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Podaci o izdanju

79

2014.

4358-4366

objavljeno

0022-3263

10.1021/jo500220h

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