226949-82-2Relevant academic research and scientific papers
A new chiral auxiliary derived from (2S)-phenylglycinol: An access to enantiomerically pure β-amino acids
Agami, Claude,Cheramy, Sandrine,Dechoux, Luc,Kadouri-Puchot, Catherine
, p. 727 - 728 (1999)
A new bicyclic heterocycle 3, which is potentially useful for the synthesis of β-amino acids, has been obtained from a reaction between (S)- phenylglycinol and cyanogen bromide followed by a condensation with methyl propiolate. Conjugate additions of different organocuprate reagents to this chiral Michael acceptor occurred with complete diastereoselectivity. An optically pure β amino acid was obtained in excellent yield from the masked chiral derivative 4a.
Enantioselective synthesis of α,β-substituted β-amino acids
Agami, Claude,Cheramy, Sandrine,Dechoux, Luc,Melaimi, Mohand
, p. 195 - 200 (2007/10/03)
Chiral derivative 3 was shown to be a precursor of α and β-substituted β-amino acids as well as α,β-disubstituted β-amino acids. The key steps of the procedure are a diastereoselective alkylation of synthon 3 by organocuprates reagents and a diastereoselective alkylation of the alkylated adduct.
