Electrophilic Amination: New Synthetic Applications

Christine Greck; Jean Pierre Genêt

doi:10.1055/s-1997-5745

Synlett 1997; 1997(7): 741-748
DOI: 10.1055/s-1997-5745

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Electrophilic Amination: New Synthetic Applications

Christine Greck¹ , Jean Pierre Genêt²

¹E.N.S.C.P., Laboratoire de Synthèse Organique, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France, Fax: (33) 1-44 07 10 62; E-mail: greck@ext.jussieu.fr
²E.N.S.C.P., Laboratoire de Synthèse Organique, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France, Fax: (33) 1-44 07 10 62; E-mail: genet@ext.jussieu.fr

Abstract

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Electrophilic aminating reagents can transfer N-protected group to carbanions or amines. N-Boc and N-Alloc protected amines or hydrazines were easily obtained using metalated t-butyl- or allyl-N-arylsulfonyloxycarbamate. N,O-Bis(trimethylsilyl) hydroxylamine or N-protected oxaziridines were reported to be convenient reagents to give N-protected derivatives.

The reaction of β-hydroxy ester enolates with the di-t-butylazodicarboxylate was a convenient entry to α-amino-β-hydroxy acids. Synthetic applications of this reaction are described.

α-amino-β-hydroxy acids - catalytic hydrogenation - electrophilic amination - N-protected amines - zinc enolate

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