Nucleophilic transformations of azido-containing carbonyl compounds via protection of the azido group

Takahiro Aimi; Tomohiro Meguro; Akihiro Kobayashi; Takamitsu Hosoya; Suguru Yoshida

doi:10.1039/D1CC01143J

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Nucleophilic transformations of azido-containing carbonyl compounds via protection of the azido group†

Takahiro Aimi,^a Tomohiro Meguro,^a Akihiro Kobayashi,^ab Takamitsu Hosoya

*^a and Suguru Yoshida

*^ab

Author affiliations

* Corresponding authors

^a Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
E-mail: s-yoshida@rs.tus.ac.jp, thosoya.cb@tmd.ac.jp

^b Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan

Abstract

Nucleophilic transformations of azido-containing carbonyl compounds are discussed. The phosphazide formation from azides and di(tert-butyl)(4-(dimethylamino)phenyl)phosphine (Amphos) enabled transformations of carbonyl groups with nucleophiles such as lithium aluminum hydride and organometallic reagents. The good stability of the phosphazide moiety allowed us to perform consecutive transformations of a diazide through triazole formation and the Grignard reaction.

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Article information

DOI: https://doi.org/10.1039/D1CC01143J
Article type: Communication
Submitted: 02 Mar 2021
Accepted: 17 May 2021
First published: 18 May 2021
This article is Open Access

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Chem. Commun., 2021,57, 6062-6065

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Nucleophilic transformations of azido-containing carbonyl compounds via protection of the azido group

T. Aimi, T. Meguro, A. Kobayashi, T. Hosoya and S. Yoshida, Chem. Commun., 2021, 57, 6062 DOI: 10.1039/D1CC01143J

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Chemical Communications

Nucleophilic transformations of azido-containing carbonyl compounds via protection of the azido group†

Abstract

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Nucleophilic transformations of azido-containing carbonyl compounds via protection of the azido group

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