Abstract
The ethynylglycine synthon {(R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyl-oxazolidine} is a chiral compound with valuable synthetic interest. An update (covering literature from 2005 to 2017) on the different synthetic utilities is reviewed and discussed.
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Abbreviations
- Ac:
-
Acetyl
- ACC synthase:
-
1-Aminocyclopropane-1-carboxylate synthase
- All:
-
Allyl
- Bn:
-
Benzyl
- Boc:
-
tert-Butoxycarbonyl
- Bu or n-Bu:
-
n-Butyl
- CAN:
-
Cerium ammonium nitrate
- Cbz:
-
Benzyloxycarbonyl
- dba:
-
Dibenzylideneacetone
- DCC:
-
N,N′-Dicyclohexylcarbodiimide
- DIBAL-H:
-
Diisobutylalumino hydride
- DIPA:
-
Diisopropylamine
- DIPEA:
-
Diisopropylethylamine
- DMAP:
-
4-Dimethylaminopyridine
- DMF:
-
Dimethylformamide
- DMP:
-
Dess–Martin periodinane
- ent-x :
-
Enantiomer of compound x
- Et:
-
Ethyl
- HMDS:
-
Hexamethyldisilazane
- IDO:
-
Indoleamine 2,3-dioxygenase
- LHMDS:
-
Lithium bis(trimethylsilyl)amide
- MCPBA:
-
m-Chloroperoxybenzoic acid
- Me:
-
Methyl
- Mts:
-
2,4,6-Trimethylbenzenesulfonyl
- MW:
-
Microwave
- NCS:
-
N-Chlorosuccinimide
- oDPPBA:
-
2-(Diphenylphosphino)benzoic acid
- oDPPB:
-
2-(Diphenylphosphino)benzoate
- Ph:
-
Phenyl
- PLP:
-
Pyridoxal phosphate
- PTSA:
-
p-Toluenesulfonic acid
- RCM:
-
Ring-closing metathesis
- SEM:
-
2-(Trimethylsilyl)ethoxymethyl
- TBAF:
-
Tetrabutylammonium fluoride
- TBAI:
-
Tetrabutylammonium iodide
- TBDMS:
-
tert-butyldimethylsilyl
- TBDPS:
-
tert-butyldiphenylsilyl
- t-Bu:
-
tert-butyl
- TEMPO:
-
2,2,6,6-Tetramethylpiperidine 1-oxyl
- TES:
-
Triethylsilyl
- Tf:
-
Triflate
- TFA:
-
Trifluoroacetic acid
- THF:
-
Tetrahydrofuran
- TMEDA:
-
N,N,N′,N′-tetramethyl ethylenediamine
- TMS:
-
Trimethylsilyl
- Ts:
-
4-toluenesulfonyl
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Benfodda, Z., Benimélis, D., Reginato, G. et al. Ethynylglycine synthon, a useful precursor for the synthesis of biologically active compounds: an update. Part II: synthetic uses of ethynylglycine synthon. Amino Acids 50, 1307–1328 (2018). https://doi.org/10.1007/s00726-018-2628-1
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DOI: https://doi.org/10.1007/s00726-018-2628-1