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Issue 26, 2018
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Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates

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Abstract

A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.

Graphical abstract: Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates

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Publication details

The article was received on 07 May 2018, accepted on 08 Jun 2018 and first published on 09 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB01061G
Citation: Org. Biomol. Chem., 2018,16, 4874-4880
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    Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates

    L. Santhosh, S. Durgamma, Shekharappa and V. V. Sureshbabu, Org. Biomol. Chem., 2018, 16, 4874
    DOI: 10.1039/C8OB01061G

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