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- W2017004248 abstract "(S)-β2-Homoamino acids with the side chains of Asp, Glu, Asn, and Gln have been prepared and suitably protected (N-Fmoc, CO2tBu, CONHTrt) for solid-phase peptide syntheses. The key steps of the syntheses are: N-acylation of 5,5-diphenyl-4-isopropyl-1,3-oxazolidin-2-one (DIOZ) with succinic and glutaric anhydrides (Scheme 2), alkylation of the corresponding Li-enolates with benzyl iodoacetate and Curtius degradation (Scheme 4), and removal of the chiral auxiliary (Scheme 5). In addition, numerous functional-group manipulations (CO2H⇌CO2tBu, CO2Bn⇌CO2H, CbzNH→FmocNH, CO2H→CO2NH2→CONHTrt; Schemes 2, 4, 5, and 6) were necessary, in order to arrive at the four target structures. The configurational assignments were confirmed by X-ray crystal-structure determinations (Scheme 2 and Fig. 3). The enantiomeric purities of a β2hAsn and of a β2hGln derivative were determined by HPLC on a Chiralcel column to be 99.7 : 0.3 and >99 : 1, respectively (Fig. 4). Notably, it took up to twelve steps to prepare a suitably protected trifunctional product with a single stereogenic center (overall yield of 10% from DIOZ and succinic anhydride)!" @default.
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- W2017004248 date "2004-06-01" @default.
- W2017004248 modified "2023-10-15" @default.
- W2017004248 title "Enantioselective Preparation ofβ2-Amino Acids with Aspartate, Glutamate, Asparagine, and Glutamine Side Chains" @default.
- W2017004248 doi "https://doi.org/10.1002/hlca.200490142" @default.
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