Synthesis of N-Protected Cyano Aziridines

Fioravanti, Stefania; Morreale, Alberto; Pellacani, Lucio; Tardella, Paolo A.

doi:10.1055/s-2004-820047

Cited by 26 publications

(20 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…1 H NMR: 1.14 (t, J¼7.7 Hz, 3H), 1.42 (s, 9H), 1.63e1.82 (m, 2H), 3.07 (t, J¼6.6 Hz, 1H), 3.77 (s, 3H), 4.08 (d, J¼6.6 Hz, 2H), 7.04e7.18 (br, 1H). 13…”

Section: Tert-butyl (2r*3r*)-2-cyano-3-ethyl-2-[(2-methoxy-2-oxoethymentioning

confidence: 99%

Solution-phase synthesis of 2-cyano and 2-amido aziridinyl peptides

et al. 2008

Self Cite

View full text Add to dashboard Cite

show abstract

“…1 H NMR: 1.14 (t, J¼7.7 Hz, 3H), 1.42 (s, 9H), 1.63e1.82 (m, 2H), 3.07 (t, J¼6.6 Hz, 1H), 3.77 (s, 3H), 4.08 (d, J¼6.6 Hz, 2H), 7.04e7.18 (br, 1H). 13…”

Section: Tert-butyl (2r*3r*)-2-cyano-3-ethyl-2-[(2-methoxy-2-oxoethymentioning

confidence: 99%

Solution-phase synthesis of 2-cyano and 2-amido aziridinyl peptides

et al. 2008

Self Cite

View full text Add to dashboard Cite

show abstract

“…Their synthesis was obtained by direct amination reaction of the corresponding (E)-acrylonitriles (Fioravanti et al 2004) using ethyl nosyloxycarbamate (NsONHCO 2 Et, Ns = 4-NO 2 C 6 H 4 SO 2 ) as the aminating agent under heterogeneous conditions (Pellacani et al 2011). The aziridination reactions take place with total retention of the starting alkene configuration.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of gem-diamino acid derivatives by a Hofmann rearrangement

et al. 2012

Self Cite

View full text Add to dashboard Cite

Starting from commercially available N-protected L-α-amino acids, N,N'-protected gem-diaminic units were obtained by a two-step methodology. A Hofmann reaction performed using a primary alcohol as the solvent to trap the isocyanate intermediate represents the key step of the new synthetic procedure. Then, the methodology was applied to α-carbamoyl α'-carboxyl aziridines, also functionalized with L-α-amino esters and stable gem-diaminic units characterized by an aziridine ring and by a retro-peptide modification were obtained. The use of the latter units in the retro-peptide chemistry allows to obtain modified peptides containing an aziridine ring able to behave as an electrophilic site and as a biomimetic structural analog of proline.

show abstract

“…For example, in the presence of calcium oxide, ethyl nosyloxycarbamate (46) functions as a nitrogen source that engages Knoevenagel adducts (e.g., 47) in aziridination (Scheme 2.13), presumably via nitrene intermediates [88]. Modest diastereoselectivities have been achieved by incorporating a menthol-derived chiral auxiliary into the carbamate reagent.…”

Section: Aziridines J17mentioning

confidence: 99%