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

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...

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Bibliographic Details
Published inTetrahedron letters Vol. 58; no. 20; pp. 1985 - 1988
Main Authors Zhang, Lianjin, Kim, Ji Hui, Jang, Doo Ok
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 17.05.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Isoindolinone
3-YLIDENEPHTHALIDES
Phthalide
SOLVENT-FREE CONDITIONS
One-pot
ALDEHYDES
SILYLATION
3-Ylidenephthalide
LEWIS-ACID CATALYSTS
Hexamethyldisilazane
ALPHA-HYDROXYPHOSPHONATES
REGIOSELECTIVE SYNTHESIS
DIMETHYL PHTHALIDE-3-PHOSPHONATES
CYCLIZATION
WATER
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Summary: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. (C) 2017 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2017.04.028