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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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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DOI: https://doi.org/10.1007/978-3-319-55621-5_2
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