The fluorenone imines of glycine esters and their phosphonic acid analogues

Shu Kobayashi, Ryo Yazaki, Kazutaka Seki, Yasuhiro Yamashita

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

(Chemical Equation Presented) Much more reactive than the corresponding benzophenone imines, which have often been used in the synthesis of α-amino acids, the title compounds undergo Mannich-type reactions with imines in the presence of a catalytic amount of a base to afford α,β-diamino acid and α,β-diaminophosphonic acid derivatives with high syn diastereoselectivity (see scheme). An asymmetric version of the reaction is also described. Boc = tert-butoxycarbonyl.

Original languageEnglish
Pages (from-to)5613-5615
Number of pages3
JournalAngewandte Chemie - International Edition
Volume47
Issue number30
DOIs
Publication statusPublished - Jul 14 2008
Externally publishedYes

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Organophosphonates
Imines
Glycine
Amino acids
Esters
Acids
Derivatives
Amino Acids
benzophenone

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

The fluorenone imines of glycine esters and their phosphonic acid analogues. / Kobayashi, Shu; Yazaki, Ryo; Seki, Kazutaka; Yamashita, Yasuhiro.

In: Angewandte Chemie - International Edition, Vol. 47, No. 30, 14.07.2008, p. 5613-5615.

Research output: Contribution to journalArticle

Kobayashi, Shu ; Yazaki, Ryo ; Seki, Kazutaka ; Yamashita, Yasuhiro. / The fluorenone imines of glycine esters and their phosphonic acid analogues. In: Angewandte Chemie - International Edition. 2008 ; Vol. 47, No. 30. pp. 5613-5615.
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