I₂/TBHP mediated diastereoselective synthesis of spiroaziridines

Abstract

A simple metal free protocol for the diastereoselective synthesis of spiroaziridines using easily accessible substrates is disclosed.

A Synthetic Overview of Enones Aziridination

“…Sasidhar and co‐workers [37] reported iodine catalyzed diastereoselective aziridination of enones ( 108 ) using different aliphatic primary amines ( 109 ) in presence of tert ‐butyl hydroperoxide (TBHP) as an oxidant in ethyl acetate or cyclohexane solvent. This process provided both simple and spiro N‐alkyl aziridines with moderate to good yields (Scheme 33).…”

“…This process produced amino-halogens, which were then cyclized via intramolecular S N 2 reaction to produce corresponding aziridines, and in most of the cases, only transaziridines were obtained. Sasidhar and co-workers [37] reported iodine catalyzed diastereoselective aziridination of enones (108) using different aliphatic primary amines (109) in presence of tert-butyl hydroperoxide (TBHP) as an oxidant in ethyl acetate or cyclohexane solvent. This process provided both simple and spiro N-alkyl aziridines with moderate to good yields (Scheme 33).…”

Recent advances in the transition metal-free synthesis of heterocycles from α,β-unsaturated ketones

“…These structural motifs are endowed with wide spectrum of biological activities. 92 Hence numerous protocols have been established till now for accessing various spiro molecules of structural complexity.…”

I2/TBHP Reagent System: A Modern Paradigm for Organic Transformations**

“…Interestingly, regardless of the substitution in substrates, trans isomer was formed as the major product, which was unambiguously confirmed by the single-crystal X-ray analysis (Scheme 67). [125] Scheme 66. Synthesis of N-alkyl spiroaziridines from primary amines and α,β-unsaturated ketones.…”

“…Interestingly, regardless of the substitution in substrates, trans isomer was formed as the major product, which was unambiguously confirmed by the single‐crystal X‐ray analysis (Scheme 67). [125] …”