Metal- and Additive-Free Intermolecular Aziridination of Olefins Using N-Boc-O-tosylhydroxylamine

Jawahar L. Jat; Dinesh Chandra; Puneet Kumar; Vikram Singh; Bhoopendra Tiwari

doi:10.1055/a-1879-7974

Synthesis, Table of Contents

Synthesis 2022; 54(20): 4513-4520
DOI: 10.1055/a-1879-7974

paper

Metal- and Additive-Free Intermolecular Aziridination of Olefins Using N-Boc-O-tosylhydroxylamine

Jawahar L. Jat ∗

^aDepartment of Chemistry, School of Physical and Decision Sciences, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow-226025, India

,

Dinesh Chandra

^aDepartment of Chemistry, School of Physical and Decision Sciences, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow-226025, India

,

Puneet Kumar

^aDepartment of Chemistry, School of Physical and Decision Sciences, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow-226025, India

,

Vikram Singh

^bDepartment of Biological and Synthetic Chemistry, Centre of Biomedical Research, SGPGIMS Campus, Raebareli Road, Lucknow-226014, India

,

Bhoopendra Tiwari ∗

^bDepartment of Biological and Synthetic Chemistry, Centre of Biomedical Research, SGPGIMS Campus, Raebareli Road, Lucknow-226014, India

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Abstract

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Abstract

A metal and additive-free stereospecific direct N-H and N-Me aziridination of inactivated olefins is disclosed using N-Boc-O-tosylhydroxylamine (TsONHBoc) as an aminating agent in hexafluoroisopropanol (HFIP). The use of TsONHBoc, which generates the free aminating agent in situ under the reaction conditions, has several inherent advantages over other similar agents, such as low cost, easy access, and stability (non-explosiveness) during storage over a longer time.

Key words

aziridination - TsONHBoc - metal and additives free - stereospecific - regioselective

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