Hypervalent silicate-assisted azidation approach for the substituted azepane motif

Bilqees Sameem; Peter Karuso; Fei Liu

doi:10.1016/j.tetlet.2022.154245

Hypervalent silicate-assisted azidation approach for the substituted azepane motif

Bilqees Sameem, Peter Karuso, Fei Liu^*

^*Corresponding author for this work

School of Natural Sciences

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

1 Citation (Scopus)

Abstract

An efficient and stereospecific azidation of a cis-disubstituted azepane is described as the first example of hypervalent silicate-assisted nucleophilic azidation on a substituted seven-membered azepane ring. DFT calculations suggest an S_N2-like mechanism whereby the azido nucleophile coordinated to the hypervalent silicate presents flexible geometries for the nucleophilic approach. The method provides a viable alternative to the classical Mitsunobu-based approaches in substituted seven-membered N-heterocycles with complex conformational properties.

Original language	English
Article number	154245
Pages (from-to)	1-5
Number of pages	5
Journal	Tetrahedron Letters
Volume	113
Early online date	17 Nov 2022
DOIs	https://doi.org/10.1016/j.tetlet.2022.154245
Publication status	Published - 21 Dec 2022

Bibliographical note

Correction citation: Bilqees Sameem, Peter Karuso, Fei Liu (2023) Erratum to “Hypervalent silicate-assisted azidation approach for the substituted azepane motif” [Tetrahedron Lett. 113C (2022) 154245], Tetrahedron Letters, Volume 117, 154383, https://doi.org/10.1016/j.tetlet.2023.154383.

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abstract = "An efficient and stereospecific azidation of a cis-disubstituted azepane is described as the first example of hypervalent silicate-assisted nucleophilic azidation on a substituted seven-membered azepane ring. DFT calculations suggest an SN2-like mechanism whereby the azido nucleophile coordinated to the hypervalent silicate presents flexible geometries for the nucleophilic approach. The method provides a viable alternative to the classical Mitsunobu-based approaches in substituted seven-membered N-heterocycles with complex conformational properties.",

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N2 - An efficient and stereospecific azidation of a cis-disubstituted azepane is described as the first example of hypervalent silicate-assisted nucleophilic azidation on a substituted seven-membered azepane ring. DFT calculations suggest an SN2-like mechanism whereby the azido nucleophile coordinated to the hypervalent silicate presents flexible geometries for the nucleophilic approach. The method provides a viable alternative to the classical Mitsunobu-based approaches in substituted seven-membered N-heterocycles with complex conformational properties.

AB - An efficient and stereospecific azidation of a cis-disubstituted azepane is described as the first example of hypervalent silicate-assisted nucleophilic azidation on a substituted seven-membered azepane ring. DFT calculations suggest an SN2-like mechanism whereby the azido nucleophile coordinated to the hypervalent silicate presents flexible geometries for the nucleophilic approach. The method provides a viable alternative to the classical Mitsunobu-based approaches in substituted seven-membered N-heterocycles with complex conformational properties.

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ER -

Hypervalent silicate-assisted azidation approach for the substituted azepane motif

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