ChemInform Abstract: Diastereoselective Synthesis of β2-Amino Acids.
Abstract
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ChemInform Abstract
A general route to β2-amino acids is presented, involving highly diastereoselective alkylation of a chiral sultam β-alaninate derivative (IV) as the key step. Alkylation must be performed below -45 °C to avoid elimination via ketene formation. β2-Homophenylalanine (VI), -homoalanine (IXa) and -homoleucine derivatives (IXb) are prepared using this technique. Starting with (-)-sultam (II), the (R)-β2-amino acids are obtained, while the corresponding (S)-enantiomers arise from (+)-sultam.
