Asymmetric electrophilic amination of chiral phosphorus-stabilized anions

Scott E. Denmark, Naoto Chatani, Sunil V. Pansare

Research output: Contribution to journalArticle

Abstract

The asymmetric electrophilic amination of phosphorus-stabilized anions derived from chiral oxazaphosphorinanes and diazaphospholidines is described. Trisyl azide is the reagent of choice for the amination process. The reaction is shown to be dependent on auxiliary structure, nature of the P-alkyl substituent and choice of amination procedure. Using the oxazaphosphorinanes 1a and cis-1e a high level of asymmetric induction can be achieved. Scalemic cis-1e provides the α-aminophosphonic acid 13 with 92% e.e. in the (S) antipode. The implications for conformation and effect of auxiliary structure on stereoselectivity are discussed.

Original languageEnglish (US)
Pages (from-to)2191-2208
Number of pages18
JournalTetrahedron
Volume48
Issue number11
DOIs
StatePublished - 1992

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Amination
Phosphorus
Anions
Stereoselectivity
Azides
Conformations
Acids

Keywords

  • Chiral Phosphorus-Stabilized Anions.
  • Electrophilic Amination
  • α-Aminophosphonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Asymmetric electrophilic amination of chiral phosphorus-stabilized anions. / Denmark, Scott E.; Chatani, Naoto; Pansare, Sunil V.

In: Tetrahedron, Vol. 48, No. 11, 1992, p. 2191-2208.

Research output: Contribution to journalArticle

Denmark, Scott E. ; Chatani, Naoto ; Pansare, Sunil V. / Asymmetric electrophilic amination of chiral phosphorus-stabilized anions. In: Tetrahedron. 1992 ; Vol. 48, No. 11. pp. 2191-2208.
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