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

Abstract

A unified approach to access Nβ-protected amino alkyl isothiocyanates from Nβ-protected amino alkyl azides through general strategy of Staudinger/aza-Wittig reaction is described.The type of protocol to access isothiocyanates depends on the availability of the precursors and also, especially in amino acid chemistry, how well the other liable groups behave towards it. Fortunately, both these factors were not of concern as precursors-azides- were prepared at ease by standard protocols and the present protocol paved the way to access title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy nullifies the need of amines to obtain title compounds, thereby, making the protocol step-economical. The added advantages include retention of chirality, convenient handling and easy purification. Few hitherto unreported compounds were also prepared and all final compounds were completely characterized by IR, mass, optical rotation, 1H and 13C NMR studies.

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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, Accepted Manuscript
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    Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates

    S. L, D. s, S. Mareppa and V. V. Suresh Babu, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8OB01061G

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