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

a   Department of Chemistry, School of Physical and Decision Sciences, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow-226025, India
,
a   Department of Chemistry, School of Physical and Decision Sciences, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow-226025, India
,
Puneet Kumar
a   Department of Chemistry, School of Physical and Decision Sciences, Babasaheb Bhimrao Ambedkar University (A Central University), Lucknow-226025, India
,
Vikram Singh
b   Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, SGPGIMS Campus, Raebareli Road, Lucknow-226014, India
,
b   Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, SGPGIMS Campus, Raebareli Road, Lucknow-226014, India
› Author Affiliations
J.L.J. thanks SERB (YSS/2015/000838) and University Grants Commission – Basic Scientific Research (UGC-BSR, No. F.30-382/2017), New Delhi, for the grants. B.T. thanks SERB, New Delhi for the financial support (CRG/2018/004424).


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.

Supporting Information



Publication History

Received: 20 May 2022

Accepted after revision: 20 June 2022

Accepted Manuscript online:
20 June 2022

Article published online:
01 August 2022

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