One-pot reaction of 2-formylbenzoates, hexamethyldisilazane, and diethyl phosphite in the presence of Yb(OTf)3: Synthesis of 3-phosphonate phthalides

[Display omitted] •One-pot reaction for the synthesis of 3-phosphonate phthalides.•One-pot reaction for the synthesis of 3-phosphonate isoindolinones.•The present reactions are highly dependent on the kind of Lewis acids. Reaction of 2-formylbenzoates with hexamethyldisilazane and diethyl phosphite...

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Bibliographic Details
Published in:Tetrahedron letters 2017-05, Vol.58 (20), p.1985-1988
Main Authors: Zhang, Lianjin, Kim, Ji Hui, Jang, Doo Ok
Format: Article
Language:English
Subjects:
3-Ylidenephthalide
Hexamethyldisilazane
Isoindolinone
One-pot
Phthalide
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Summary:[Display omitted] •One-pot reaction for the synthesis of 3-phosphonate phthalides.•One-pot reaction for the synthesis of 3-phosphonate isoindolinones.•The present reactions are highly dependent on the kind of Lewis acids. Reaction of 2-formylbenzoates with hexamethyldisilazane and diethyl phosphite in the presence of Yb(OTf)3 proceeded smoothly at room temperature to afford addition adducts, which were readily cyclized to 3-phosphonate phthalides by adding trifluoroacetic acid (TFA). The reactions employing Sc(OTf)3 instead of Yb(OTf)3 produced 3-phosphonate isoindolinones without addition of TFA.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.04.028