Synthesis 2018; 50(18): 3571-3588
DOI: 10.1055/s-0036-1591600
review
© Georg Thieme Verlag Stuttgart · New York

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

Loránd Kiss*
a  Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary   Email: kiss.lorand@pharm.u-szeged.hu
,
Márton Kardos
a  Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary   Email: kiss.lorand@pharm.u-szeged.hu
,
Csaba Vass
a  Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary   Email: kiss.lorand@pharm.u-szeged.hu
,
Ferenc Fülöp
a  Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary   Email: kiss.lorand@pharm.u-szeged.hu
b  MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, 6720 Szeged, Eötvös u. 6, Hungary
› Author Affiliations
Further Information

Publication History

Received: 19 April 2018

Accepted after revision: 14 May 2018

Publication Date:
26 July 2018 (eFirst)

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

 
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