Sterically hindered C α, α-disubstituted α-amino acids: Synthesis from α-nitroacetate and incorporation into peptides

…, TJ Miller, FR Fronczek, ML McLaughlin…

Index: Fu; Hammarstroem; Miller; Fronczek; McLaughlin; Hammer Journal of Organic Chemistry, 2001 , vol. 66, # 21 p. 7118 - 7124

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Citation Number: 50

Abstract

The preparation of sterically hindered and polyfunctional C α, α-disubstituted α-amino acids (ααAAs) via alkylation of ethyl nitroacetate and transformation into derivatives ready for incorporation into peptides are described. Treatment of ethyl nitroacetate with N, N- diisopropylethylamine (DIEA) in the presence of a catalytic amount of tetraalkylammonium salt, followed by the addition of an activated alkyl halide or Michael acceptor, gives the ...

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