Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides

Takahiro Soeta; Suguru Takashita; Yoko Sakata; Yutaka Ukaji

doi:10.1039/C5OB02032H

Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides

Takahiro Soeta,*^a Suguru Takashita,^a Yoko Sakata^a and Yutaka Ukaji*^a

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* Corresponding authors

^a Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa 920-1192, Japan
E-mail: soeta@se.kanazawa-u.ac.jp, ukaji@staff.kanazawa-u.ac.jp

Abstract

The reaction of (Z)-hydroximoyl chlorides with isocyanides promoted by phosphinic acid in the presence of triethylamine proceeds smoothly to afford α-(hydroxyimino)amides in good to high yields. Phosphinic acid plays an important role in effectively promoting the reaction. A wide range of (Z)-hydroximoyl chlorides and isocyanides were found to be suitable for this reaction.

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Publication details

The article was received on 30 Sep 2015, accepted on 30 Oct 2015 and first published on 30 Oct 2015

Article type: Paper

DOI: 10.1039/C5OB02032H

Author version available: Download Author version (PDF)

Citation: Org. Biomol. Chem., 2016,14, 694-700

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Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides

T. Soeta, S. Takashita, Y. Sakata and Y. Ukaji, Org. Biomol. Chem., 2016, 14, 694
DOI: 10.1039/C5OB02032H
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Organic & Biomolecular Chemistry

Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides

Abstract

Supplementary files

Publication details

Phosphinic acid-promoted addition reaction of isocyanides to (Z)-hydroximoyl chlorides: efficient synthesis of α-(hydroxyimino)amides

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