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Role of Transition Metal Reagents in β-Lactam Synthesis: New Paradigms

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Abstract

2-Azetidinones or β-lactams constitutes a well acknowledged class of antibiotics for about 80 years. The synthetic and biological aspects have attracted considerable interest of the research community around the world. Their applications as key synthons for biologically active natural/unnatural compounds, valuable building blocks and diverse pharmacological activities have accelerated the efforts in β-lactam synthesis. In this regard, transition metal reagents have provided enormous opportunities for revealing novel and selective approaches for the preparation of these heterocycles. Present chapter reviews the recent developments (2005–2015) made in β-lactams synthesis using various transition metal reagents. The introductory paragraph highlights the significance of the β-lactams chemistry followed by an overview of general synthetic methodologies of β-lactam synthesis. The other sections of this article deal with the various synthetic methodologies using transition metal reagents.

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Abbreviations

Å:

Angstrom

Ac:

Acetyl

Ar:

Aryl

Bu:

Butyl

iBu:

Iso-Butyl

tBu:

Tert-Butyl

Bn/Bz:

Benzyl

[bmIm]:

1-Butyl-3-methylimidazolium

°C:

Degree centigrade

CAC:

Chloroacetyl chloride

Cbz:

Carboxybenzyl

CHCl3 :

Chloroform

CO:

Carbon monoxide

Cy2NH:

Dicyclohexylamine

Dba:

Dibenzylideneacetone

D:

Deuterium

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCM:

Dichloromethane

DME:

Dimethoxyethane

DMF:

N,N-Dimethylformamide

DMSO:

Dimethylsulfoxide

De :

Distereomeric excess

Ee :

Enantiomeric excess

Et:

Ethyl

ERGs:

Electron releasing groups

EWGs:

Electron withdrawing groups

G:

Gram

H:

Hour

LDA:

Lithium diisopropylamide

MeOH:

Methyl alcohol

MWI:

Microwave irradiation

Μg:

Microgram

Min:

Minute

mL:

Millilitre

mmol:

Millimole

Me:

Methyl

Ms:

Mesylate

NCS:

N-Chlorosuccinimide

Nu:

Nucleophile

Ph:

Phenyl

Piv:

Pivaloyl

Pr:

Propyl

iPr:

Iso-Propyl

PMB:

P-Methoxybenzyl

PMP:

P-Methoxyphenyl

Ppm:

Parts per million

SDS:

Sodium dodecyl sulphate

TBS:

Tert-Butyldimethylsilyl ether

TBDPS:

Tert-Butyldiphenylsilyl ether

ThP:

Thiophene

TMSCl:

Trimethylsilyl chloride

TMSQD:

Trimethylsilylquinidine

Tr:

Trityl

Ts:

Tosyl

p-TSA:

P-Toluenesulfonic acid

THF:

Tetrahydrofuran

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Authors and Affiliations

  1. Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh, 160 014, India

    Shamsher S. Bari, Aman Bhalla & Jitender Bhalla

Authors
  1. Shamsher S. Bari
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  2. Aman Bhalla
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  3. Jitender Bhalla
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Corresponding author

Correspondence to Shamsher S. Bari .

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Editors and Affiliations

  1. Community Health System of South Texas, Edinburg, Texas, USA

    Bimal K. Banik

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Bari, S.S., Bhalla, A., Bhalla, J. (2017). Role of Transition Metal Reagents in β-Lactam Synthesis: New Paradigms. In: Banik, B. (eds) Beta-Lactams. Springer, Cham. https://doi.org/10.1007/978-3-319-55621-5_2

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