Issue 13, 1993
From the journal:

Journal of the Chemical Society, Chemical Communications

N-phthalimidoaziridines by diastereoselective Addition to α,β-unsaturated amides: a route to chiral β-substituted α-hydrazino acid derivatives

James T. Kapron,   Bernard D. Santarsiero  and  John C. Vederas  

Abstract

Lead tetraacetate oxidation of N-aminophthalimide 1 in the presence of N-enoylbornane[10,2]sultams (Oppolzer auxiliary) generates corresponding N-phthalimidoaziridine adducts (12–94% yield) with 33% to [gt-or-equal]95% diastereofacial selectivity (syn attack at the re face of the α-carbon for 4a); these chiral N-aminoaziridine derivatives readily undergo ring opening by sulfur nucleophiles to give α-hydrazino acid derivatives.

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Article information

DOI
https://doi.org/10.1039/C39930001074
Article type
Paper

J. Chem. Soc., Chem. Commun., 1993, 1074-1076

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N-phthalimidoaziridines by diastereoselective Addition to α,β-unsaturated amides: a route to chiral β-substituted α-hydrazino acid derivatives

J. T. Kapron, B. D. Santarsiero and J. C. Vederas, J. Chem. Soc., Chem. Commun., 1993, 1074 DOI: 10.1039/C39930001074

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