Stereocontrolled Synthesis of Difunctionalized Azetidinones and β2,3-Amino Acid Derivatives from Cyclodienes by Ring-Opening and Cross-Metathesis Reactions

Márton Kardos, L. Kiss, F. Fülöp

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A stereocontrolled approach to highly functionalized 3,4-disubstituted azetidin-2-ones and β2,3-amino acid derivatives from readily available cycloalkadienes was achieved. The syntheses involved 1,3-dipolar cycloaddition of chlorosulfonyl isocyanate, followed by ring-opening metathesis of the unsaturated bi- or tricyclic β-lactams, and cross-metathesis of the resulting divinyl-substituted azetidinones. The substituted lactams were subsequently transformed by heteroring-opening into the corresponding functionalized acyclic β2,3-amino acid derivatives.

Original languageEnglish
Pages (from-to)1155-1159
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume4
Issue number10
DOIs
Publication statusPublished - Oct 1 2015

Fingerprint

Lactams
Derivatives
Amino Acids
Cycloaddition
2-azetidinone
chlorosulfonyl isocyanate
1,3-butadiene

Keywords

  • Amino acids
  • Azetidin-2-ones
  • Cycloalkadienes
  • Metathesis
  • β-lactams

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Stereocontrolled Synthesis of Difunctionalized Azetidinones and β2,3-Amino Acid Derivatives from Cyclodienes by Ring-Opening and Cross-Metathesis Reactions",
abstract = "A stereocontrolled approach to highly functionalized 3,4-disubstituted azetidin-2-ones and β2,3-amino acid derivatives from readily available cycloalkadienes was achieved. The syntheses involved 1,3-dipolar cycloaddition of chlorosulfonyl isocyanate, followed by ring-opening metathesis of the unsaturated bi- or tricyclic β-lactams, and cross-metathesis of the resulting divinyl-substituted azetidinones. The substituted lactams were subsequently transformed by heteroring-opening into the corresponding functionalized acyclic β2,3-amino acid derivatives.",
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T1 - Stereocontrolled Synthesis of Difunctionalized Azetidinones and β2,3-Amino Acid Derivatives from Cyclodienes by Ring-Opening and Cross-Metathesis Reactions

AU - Kardos, Márton

AU - Kiss, L.

AU - Fülöp, F.

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N2 - A stereocontrolled approach to highly functionalized 3,4-disubstituted azetidin-2-ones and β2,3-amino acid derivatives from readily available cycloalkadienes was achieved. The syntheses involved 1,3-dipolar cycloaddition of chlorosulfonyl isocyanate, followed by ring-opening metathesis of the unsaturated bi- or tricyclic β-lactams, and cross-metathesis of the resulting divinyl-substituted azetidinones. The substituted lactams were subsequently transformed by heteroring-opening into the corresponding functionalized acyclic β2,3-amino acid derivatives.

AB - A stereocontrolled approach to highly functionalized 3,4-disubstituted azetidin-2-ones and β2,3-amino acid derivatives from readily available cycloalkadienes was achieved. The syntheses involved 1,3-dipolar cycloaddition of chlorosulfonyl isocyanate, followed by ring-opening metathesis of the unsaturated bi- or tricyclic β-lactams, and cross-metathesis of the resulting divinyl-substituted azetidinones. The substituted lactams were subsequently transformed by heteroring-opening into the corresponding functionalized acyclic β2,3-amino acid derivatives.

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