Dehydrative cyclization of serine, threonine, and cysteine residues catalyzed by molybdenum(VI) oxo compounds

Akira Sakakura, Rei Kondo, Shuhei Umemura, Kazuaki Ishihara

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Commercially available molybdenum(VI) oxides such as (NH4)2MoO4, (NH4)6Mo7O24·4H2O, MoO2(acac)2, and MoO2(TMHD)2 are highly effective dehydrative cyclization catalysts for the synthesis of a variety of oxazolines. The reaction proceeds with a complete retention of configuration at the β-position. For the dehydrative cyclization of cysteine derivatives, bis(2-ethyl-8-quinolinolato)dioxomolybdenum(VI) shows remarkable catalytic activity and gives thiazolines without a significant loss of stereochemical integrity at the C2-exomethine positions.

Original languageEnglish
Pages (from-to)2102-2109
Number of pages8
JournalTetrahedron
Volume65
Issue number10
DOIs
Publication statusPublished - Mar 7 2009
Externally publishedYes

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Molybdenum
Cyclization
Threonine
Serine
Cysteine
Oxides
Catalyst activity
Derivatives
Catalysts
molybdenum dioxide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Dehydrative cyclization of serine, threonine, and cysteine residues catalyzed by molybdenum(VI) oxo compounds. / Sakakura, Akira; Kondo, Rei; Umemura, Shuhei; Ishihara, Kazuaki.

In: Tetrahedron, Vol. 65, No. 10, 07.03.2009, p. 2102-2109.

Research output: Contribution to journalArticle

Sakakura, Akira ; Kondo, Rei ; Umemura, Shuhei ; Ishihara, Kazuaki. / Dehydrative cyclization of serine, threonine, and cysteine residues catalyzed by molybdenum(VI) oxo compounds. In: Tetrahedron. 2009 ; Vol. 65, No. 10. pp. 2102-2109.
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