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

Lianjin Zhang; Ji Hui Kim; Doo Ok Jang

doi:10.1016/j.tetlet.2017.04.028

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

Lianjin Zhang, Ji Hui Kim, Doo Ok Jang

Chemistry and Medical Chemistry

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1985-1988
Number of pages	4
Journal	Tetrahedron Letters
Volume	58
Issue number	20
DOIs	https://doi.org/10.1016/j.tetlet.2017.04.028
Publication status	Published - 2017

Bibliographical note

Publisher Copyright:
© 2017 Elsevier Ltd

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2017.04.028

Cite this

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

abstract = "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.",

author = "Lianjin Zhang and Kim, {Ji Hui} and Jang, {Doo Ok}",

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journal = "Tetrahedron Letters",

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AU - Zhang, Lianjin

AU - Kim, Ji Hui

AU - Jang, Doo Ok

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AB - 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.

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