Download PDF
Synlett 1997; 1997(7): 741-748
DOI: 10.1055/s-1997-5745
account
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >