Beilstein J. Org. Chem.2009,5, No. 43, doi:10.3762/bjoc.5.43
ofstereocentres (SRS); Introduction
Monosubstituted β-amino carboxylic acids can be classified according to their substitution pattern into α-substituted “β2-amino acids” and β-substituted “β3-amino acids” [1]. Oligomers of these β-amino acids are called “β-peptides” and tend to form distinct and
. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R)-β2-homoaspartate.
Keywords: β2-amino acids; cyclocondensation; diastereoselective alkylation; N,N-acetals; peptidomimetics; ring opening; self-regeneration
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Graphical Abstract
Scheme 1:
Selectively cleavable β2-amino acid precursors: Structures and reactivities of 2-tert-butyl-tetrahy...