Multinuclear magnetic resonance study of oxaziridines

Abstract

NMR data ("C, "N, "O) for the three ring atoms of various oxaziridines are compared. Tbeir significance for the prediction of the enantioselectivity of the oxidation of sulphides by chiral oxaziridines is discussed.

Structural and conformational analysis of 1‐oxaspiro[2.5]octane and 1‐oxa‐2‐azaspiro[2.5]octane derivatives by 1H, 13C, and 15N NMR

“…The chemical shifts determined here were similar to those previously reported . The N‐C 6 H 5 and N‐CH 2 CH 2 CH 3 derivatives did not display significant differences in the chemical shifts of 15 N (Δδ N < 1.4 derivative 2 with 4 ) and the coupling constant 2/3 J N‐H (ΔJ < 1.4).…”

Hydrogen peroxide/dimethyl carbonate: a green system for epoxidation of N-alkylimines and N-sulfonylimines. One-pot synthesis of N-alkyloxaziridines from N-alkylamines and (hetero)aromatic aldehydes

“…These stereoselectivity results are in agreement with the other methods described in the literature. 17,22,43,44 The one-pot synthesis of N-alkyloxaziridines, described in this work, provided a high stereoselectivity, affording the trans-isomer as a major product (100 : 0-90 : 10, Table 2). The cis/trans ratio was determined by 1 H NMR analysis.…”

“…Indeed, cis and trans-oxaziridines isomers are known to give different 1 H and 13 C NMR spectra. 17,22,43,44 NMR data of cis and trans-oxaziridines isomers is provided in ESI. † Encouraged by the excellent results obtained using the H 2 O 2 /DMC system for the synthesis of N-alkyloxaziridines, we investigated the preparation of other synthetically important oxaziridines, such as N-sulfonyloxaziridines.…”

Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

“…This versatile intermediate can be reduced to provide a chelating ligand for chiral catalysis [16], or oxidised to oxaziridines used as efficient chiral oxidising reagents [13,17–19]. …”

“…From cheap camphor-10-sulfonic acid ( 1 ), a cyclic sulfonimide 2 can easily be obtained which is readily converted into useful auxiliaries [ 12 ], or oxidized to the oxoimide 3 ( Scheme 1 ) [ 13 – 15 ]. This versatile intermediate can be reduced to provide a chelating ligand for chiral catalysis [ 16 ], or oxidised to oxaziridines used as efficient chiral oxidising reagents [ 13 , 17 – 19 ].…”