Chemistry involves the study of all things chemical – chemical processes, chemical compositions and chemical manipulation – in order to better understand the way in which materials are structured, how they change and how they react in certain situations. Application In Synthesis of (S)-4-Isopropyl-5,5-diphenyloxazolidin-2-one
In view of the prominent role of the 1H-indol-3-yl side chain of tryptophan in peptides and proteins, it is important to have the appropriately protected homologs H-beta2-HTrp-OH and H-beta3-HTrp-OH (Fig.) available for incorporation in beta-peptides. The beta2-HTrp building block is especially important, because beta2-amino acid residues cause beta-peptide chains to fold to the unusual 12/10 helix or to a hairpin turn. The preparation of Fmoc- and Z-beta2-HTrp(Boc)-OH by Curtius degradation (Scheme 1) of a succinic acid derivative is described (Schemes 2 – 4). To this end, the (S)-4-isopropyl-3-[(N-Boc-indol-3-yl)propionyl]-1,3-oxazolidin-2-one enolate is alkylated with Br-CH2CO2Bn (Scheme 3). Subsequent hydrogenolysis, Curtius degradation, and removal of the Evans auxiliary group gives the desired derivatives of (R)-H-beta2-HTrp-OH (Scheme 4). Since the (R)-form of the auxiliary is also available, access to (S)-beta2-HTrp-containing beta-peptides is provided as well.
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Reference：
Oxazolidine – Wikipedia,
Oxazolidine | C3H2640NO – PubChem