Application of Metathesis Reactions in the Synthesis and Transformations of Functionalized β-Amino Acid Derivatives

L. Kiss, Márton Kardos, Csaba Vass, F. Fülöp

Research output: Contribution to journalReview article

4 Citations (Scopus)

Abstract

Because of their biological relevance, cyclic β-amino acids have generated increasing interest and had significant impact in drug research over the past two decades. Their preparation and further functionalization towards new types of molecular entities have received large interest in synthetic and medicinal chemistry. Various types of metathesis reactions, such as ring-opening (ROM), ring-closing (RCM), or cross metathesis (CM) are used widely for access to either alicyclic β-amino acids or other densely functionalized derivatives of this group of compounds. This account intends to provide an insight into the most relevant synthetic routes to this class of derivatives with the application of metathesis reactions. The review focuses on the presentation of selective and stereocontrolled methodologies in view of versatility, robustness, limitations and efficiency. 1 Introduction 2 Synthesis and Transformation of Cyclic β-Amino Acids through Metathesis Reactions 2.1 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Ring-Closing Metathesis 2.2 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Cross Metathesis 2.3 Synthesis of β-Amino Acids with Larger Ring Systems by Ring- Closing Metathesis 2.4 Synthesis of β-Amino Acids with Condensed Ring Systems by Ring-Rearrangement Metathesis 2.5 Stereocontrolled One-Step Synthesis of Functionalized Cispentacin and Transpentacin Derivatives 2.5.1 Stereocontrolled Synthesis of Functionalized Cispentacin and Transpentacin Derivatives through Ring-Opening Metathesis of Norbornene β-Amino Acid Derivatives 2.5.2 Stereocontrolled Synthesis of Functionalized Azetidinones and β-Amino Acid Derivatives from Condensed Ring β-Lactams by Ring-Opening Metathesis 2.5.3 Carbon-Carbon Double Bond Functionalization of β-Amino Acid Derivatives and β-Lactams with α,β-Unsaturated Carbonyl Compounds through Cross Metathesis 2.5.4 Synthesis of Functionalized β-Amino Acid Derivatives and β-Lactams through Chemoselective Cross Metathesis 3 Conclusions and Outlook.

Original languageEnglish
Article numberss-2018-e0261-r
Pages (from-to)3571-3588
Number of pages18
JournalSynthesis (Germany)
Volume50
Issue number18
DOIs
Publication statusPublished - Jan 1 2018

Fingerprint

Amino acids
Cyclic Amino Acids
Derivatives
Amino Acids
Lactams
Carbon
Carbonyl compounds
ROM
Pharmaceutical Preparations

Keywords

  • amino acids
  • heterocycles
  • metathesis
  • ring closure
  • stereoselectivity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Application of Metathesis Reactions in the Synthesis and Transformations of Functionalized β-Amino Acid Derivatives. / Kiss, L.; Kardos, Márton; Vass, Csaba; Fülöp, F.

In: Synthesis (Germany), Vol. 50, No. 18, ss-2018-e0261-r, 01.01.2018, p. 3571-3588.

Research output: Contribution to journalReview article

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AB - Because of their biological relevance, cyclic β-amino acids have generated increasing interest and had significant impact in drug research over the past two decades. Their preparation and further functionalization towards new types of molecular entities have received large interest in synthetic and medicinal chemistry. Various types of metathesis reactions, such as ring-opening (ROM), ring-closing (RCM), or cross metathesis (CM) are used widely for access to either alicyclic β-amino acids or other densely functionalized derivatives of this group of compounds. This account intends to provide an insight into the most relevant synthetic routes to this class of derivatives with the application of metathesis reactions. The review focuses on the presentation of selective and stereocontrolled methodologies in view of versatility, robustness, limitations and efficiency. 1 Introduction 2 Synthesis and Transformation of Cyclic β-Amino Acids through Metathesis Reactions 2.1 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Ring-Closing Metathesis 2.2 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Cross Metathesis 2.3 Synthesis of β-Amino Acids with Larger Ring Systems by Ring- Closing Metathesis 2.4 Synthesis of β-Amino Acids with Condensed Ring Systems by Ring-Rearrangement Metathesis 2.5 Stereocontrolled One-Step Synthesis of Functionalized Cispentacin and Transpentacin Derivatives 2.5.1 Stereocontrolled Synthesis of Functionalized Cispentacin and Transpentacin Derivatives through Ring-Opening Metathesis of Norbornene β-Amino Acid Derivatives 2.5.2 Stereocontrolled Synthesis of Functionalized Azetidinones and β-Amino Acid Derivatives from Condensed Ring β-Lactams by Ring-Opening Metathesis 2.5.3 Carbon-Carbon Double Bond Functionalization of β-Amino Acid Derivatives and β-Lactams with α,β-Unsaturated Carbonyl Compounds through Cross Metathesis 2.5.4 Synthesis of Functionalized β-Amino Acid Derivatives and β-Lactams through Chemoselective Cross Metathesis 3 Conclusions and Outlook.

KW - amino acids

KW - heterocycles

KW - metathesis

KW - ring closure

KW - stereoselectivity

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